{"id":"https://openalex.org/W5594782","doi":"https://doi.org/10.7907/wyag-4s28","title":"Forays into the Synthesis of Zoanthenol: Intriguing Patterns in Reactivity and Selectivity","display_name":"Forays into the Synthesis of Zoanthenol: Intriguing Patterns in Reactivity and Selectivity","publication_year":2009,"publication_date":"2009-02-05","ids":{"openalex":"https://openalex.org/W5594782","doi":"https://doi.org/10.7907/wyag-4s28","mag":"5594782"},"language":"en","primary_location":{"id":"pmh:oai:thesis.library.caltech.edu:5","doi":null,"is_oa":true,"landing_page_url":"https://thesis.library.caltech.edu/5/20/20_AppDSpectra.doc","pdf_url":"https://thesis.library.caltech.edu/5/1/01_CoverPage.pdf","source":{"id":"https://openalex.org/S4306402402","display_name":"CaltechTHESIS (California Institute of Technology)","issn_l":null,"issn":null,"is_oa":false,"is_in_doaj":false,"is_core":false,"listed_in":[],"host_organization":"https://openalex.org/I122411786","host_organization_name":"California Institute of Technology","host_organization_lineage":["https://openalex.org/I122411786"],"host_organization_lineage_names":[],"type":"repository"},"license":null,"license_id":null,"version":"submittedVersion","is_accepted":false,"is_published":false,"raw_source_name":"","raw_type":"Thesis"},"volume":null,"type":"dissertation","indexed_in":["datacite"],"open_access":{"is_oa":true,"oa_status":"green","oa_url":"https://thesis.library.caltech.edu/5/1/01_CoverPage.pdf","any_repository_has_fulltext":true},"authorships":[{"author_position":"first","author":{"id":"https://openalex.org/A5055010269","display_name":"Jennifer L. Stockdill","orcid":"https://orcid.org/0000-0003-4238-6530","observed_orcids":["https://orcid.org/0000-0003-4238-6530"]},"institutions":[{"id":"https://openalex.org/I122411786","display_name":"California Institute of Technology","ror":"https://ror.org/05dxps055","country_code":"US","type":"education","lineage":["https://openalex.org/I122411786"]}],"countries":["US"],"is_corresponding":true,"raw_author_name":"Stockdill, Jennifer Lynn","raw_affiliation_strings":["California Institute of Technology"],"raw_orcid":"https://orcid.org/0000-0003-4238-6530","affiliations":[{"raw_affiliation_string":"California Institute of Technology","institution_ids":["https://openalex.org/I122411786"]}]}],"institutions":[],"countries_distinct_count":1,"institutions_distinct_count":1,"corresponding_author_ids":["https://openalex.org/A5055010269"],"corresponding_institution_ids":["https://openalex.org/I122411786"],"apc_list":null,"apc_paid":null,"fwci":null,"has_fulltext":false,"cited_by_count":0,"citation_normalized_percentile":null,"cited_by_percentile_year":null,"biblio":{"volume":null,"issue":null,"first_page":null,"last_page":null},"is_retracted":false,"is_paratext":false,"is_xpac":false,"primary_topic":{"id":"https://openalex.org/T13649","display_name":"Advanced Synthetic Organic Chemistry","score":0.9175000190734863,"subfield":{"id":"https://openalex.org/subfields/1605","display_name":"Organic Chemistry"},"field":{"id":"https://openalex.org/fields/16","display_name":"Chemistry"},"domain":{"id":"https://openalex.org/domains/3","display_name":"Physical Sciences"}},"topics":[{"id":"https://openalex.org/T13649","display_name":"Advanced Synthetic Organic Chemistry","score":0.9175000190734863,"subfield":{"id":"https://openalex.org/subfields/1605","display_name":"Organic Chemistry"},"field":{"id":"https://openalex.org/fields/16","display_name":"Chemistry"},"domain":{"id":"https://openalex.org/domains/3","display_name":"Physical Sciences"}},{"id":"https://openalex.org/T13971","display_name":"Synthesis and Biological Activity","score":0.03779999911785126,"subfield":{"id":"https://openalex.org/subfields/1306","display_name":"Cancer Research"},"field":{"id":"https://openalex.org/fields/13","display_name":"Biochemistry, Genetics and Molecular Biology"},"domain":{"id":"https://openalex.org/domains/1","display_name":"Life Sciences"}},{"id":"https://openalex.org/T13859","display_name":"Organic Chemistry Synthesis Methods","score":0.028300000354647636,"subfield":{"id":"https://openalex.org/subfields/1605","display_name":"Organic Chemistry"},"field":{"id":"https://openalex.org/fields/16","display_name":"Chemistry"},"domain":{"id":"https://openalex.org/domains/3","display_name":"Physical Sciences"}}],"keywords":[{"id":"https://openalex.org/keywords/total-synthesis","display_name":"total synthesis","score":0.9279999732971191},{"id":"https://openalex.org/keywords/tricyclic-core","display_name":"tricyclic core","score":0.7329999804496765},{"id":"https://openalex.org/keywords/quaternary-stereocenters","display_name":"quaternary stereocenters","score":0.7960000038146973},{"id":"https://openalex.org/keywords/friedel-crafts-cyclization","display_name":"Friedel-Crafts cyclization","score":0.953000009059906},{"id":"https://openalex.org/keywords/radical-cyclization","display_name":"radical cyclization","score":0.7580000162124634},{"id":"https://openalex.org/keywords/stereoselectivity","display_name":"stereoselectivity","score":0.6499999761581421},{"id":"https://openalex.org/keywords/reactivity-patterns","display_name":"reactivity patterns","score":0.5199999809265137}],"concepts":[{"id":"https://openalex.org/C40869318","wikidata":"https://www.wikidata.org/wiki/Q899050","display_name":"Synthon","level":2,"score":0.9060190916061401},{"id":"https://openalex.org/C134195300","wikidata":"https://www.wikidata.org/wiki/Q902071","display_name":"Stereocenter","level":4,"score":0.8242511749267578},{"id":"https://openalex.org/C185592680","wikidata":"https://www.wikidata.org/wiki/Q2329","display_name":"Chemistry","level":0,"score":0.6625756025314331},{"id":"https://openalex.org/C2780378348","wikidata":"https://www.wikidata.org/wiki/Q25351438","display_name":"Ring (chemistry)","level":2,"score":0.631423830986023},{"id":"https://openalex.org/C71240020","wikidata":"https://www.wikidata.org/wiki/Q186011","display_name":"Stereochemistry","level":1,"score":0.5852768421173096},{"id":"https://openalex.org/C35753019","wikidata":"https://www.wikidata.org/wiki/Q644785","display_name":"Total synthesis","level":2,"score":0.5524343252182007},{"id":"https://openalex.org/C20327893","wikidata":"https://www.wikidata.org/wiki/Q7280479","display_name":"Radical cyclization","level":2,"score":0.4980475902557373},{"id":"https://openalex.org/C21951064","wikidata":"https://www.wikidata.org/wiki/Q899212","display_name":"Combinatorial chemistry","level":1,"score":0.44683837890625},{"id":"https://openalex.org/C146686406","wikidata":"https://www.wikidata.org/wiki/Q898628","display_name":"Enantioselective synthesis","level":3,"score":0.3000713586807251},{"id":"https://openalex.org/C178790620","wikidata":"https://www.wikidata.org/wiki/Q11351","display_name":"Organic chemistry","level":1,"score":0.23689326643943787},{"id":"https://openalex.org/C161790260","wikidata":"https://www.wikidata.org/wiki/Q82264","display_name":"Catalysis","level":2,"score":0.07802751660346985}],"mesh":[],"locations_count":3,"locations":[{"id":"pmh:oai:thesis.library.caltech.edu:5","doi":null,"is_oa":true,"landing_page_url":"https://thesis.library.caltech.edu/5/20/20_AppDSpectra.doc","pdf_url":"https://thesis.library.caltech.edu/5/1/01_CoverPage.pdf","source":{"id":"https://openalex.org/S4306402402","display_name":"CaltechTHESIS (California Institute of Technology)","issn_l":null,"issn":null,"is_oa":false,"is_in_doaj":false,"is_core":false,"listed_in":[],"host_organization":"https://openalex.org/I122411786","host_organization_name":"California Institute of Technology","host_organization_lineage":["https://openalex.org/I122411786"],"host_organization_lineage_names":[],"type":"repository"},"license":null,"license_id":null,"version":"submittedVersion","is_accepted":false,"is_published":false,"raw_source_name":"","raw_type":"Thesis"},{"id":"mag:5594782","doi":null,"is_oa":false,"landing_page_url":"http://resolver.caltech.edu/CaltechETD:etd-01022009-165956","pdf_url":null,"source":null,"license":null,"license_id":null,"version":null,"is_accepted":false,"is_published":false,"raw_source_name":null,"raw_type":null},{"id":"doi:10.7907/wyag-4s28","doi":"https://doi.org/10.7907/wyag-4s28","is_oa":true,"landing_page_url":"https://doi.org/10.7907/wyag-4s28","pdf_url":null,"source":{"id":"https://openalex.org/S7407050848","display_name":"Caltech Library","issn_l":null,"issn":null,"is_oa":false,"is_in_doaj":false,"is_core":false,"listed_in":[],"host_organization":"https://openalex.org/I122411786","host_organization_name":"California Institute of Technology","host_organization_lineage":["https://openalex.org/I122411786"],"host_organization_lineage_names":[],"type":"repository"},"license":null,"license_id":null,"version":null,"is_accepted":false,"is_published":false,"raw_source_name":null,"raw_type":"thesis"}],"best_oa_location":{"id":"pmh:oai:thesis.library.caltech.edu:5","doi":null,"is_oa":true,"landing_page_url":"https://thesis.library.caltech.edu/5/20/20_AppDSpectra.doc","pdf_url":"https://thesis.library.caltech.edu/5/1/01_CoverPage.pdf","source":{"id":"https://openalex.org/S4306402402","display_name":"CaltechTHESIS (California Institute of Technology)","issn_l":null,"issn":null,"is_oa":false,"is_in_doaj":false,"is_core":false,"listed_in":[],"host_organization":"https://openalex.org/I122411786","host_organization_name":"California Institute of Technology","host_organization_lineage":["https://openalex.org/I122411786"],"host_organization_lineage_names":[],"type":"repository"},"license":null,"license_id":null,"version":"submittedVersion","is_accepted":false,"is_published":false,"raw_source_name":"","raw_type":"Thesis"},"sustainable_development_goals":[],"sustainable_development_goals_aurora":[],"study_designs":[],"awards":[],"funders":[],"has_content":{"pdf":true,"grobid_xml":false},"content_urls":{"pdf":"https://content.openalex.org/works/W5594782.pdf"},"referenced_works_count":0,"referenced_works":[],"related_works":["https://openalex.org/W934083600","https://openalex.org/W1987859831","https://openalex.org/W2121242988","https://openalex.org/W2315071154","https://openalex.org/W2331285589","https://openalex.org/W3151214185","https://openalex.org/W2077876471","https://openalex.org/W7097029004","https://openalex.org/W2951631489","https://openalex.org/W2034313662"],"abstract_inverted_index":{"The":[0,107],"zoanthamine":[1],"family":[2,105],"of":[3,9,21,53,91,119,130,169,212,237],"alkaloids":[4],"has":[5],"attracted":[6],"the":[7,18,49,59,87,103,116,127,131,136,146,166,170,180,188,199,228,233,238,246,258],"attention":[8,176],"synthetic":[10,108],"chemists":[11],"for":[12,97,278],"over":[13],"two":[14,239],"decades,":[15],"beginning":[16],"with":[17,204],"first":[19],"report":[20],"their":[22],"isolation":[23],"in":[24,72,145,207,245,264],"1984.":[25],"Not":[26],"only":[27,60],"are":[28,153,173,243,272,281],"these":[29,47,249,265],"stereochemically":[30],"dense":[31],"polycyclic":[32],"compounds":[33],"structurally":[34,81],"fascinating,":[35],"but":[36],"they":[37],"also":[38],"display":[39],"interesting":[40],"and":[41,70,162,231,262,274],"important":[42],"biological":[43],"activities.":[44],"Foremost":[45],"among":[46],"is":[48,142,177,196,202],"potent":[50],"anti-osteoporotic":[51],"effect":[52],"norzoanthamine.":[54],"To":[55],"date,":[56],"norzoanthamine":[57],"remains":[58],"member":[61],"to":[62,65,102,115,156,164,179,187,209,226],"have":[63,252],"succumbed":[64],"total":[66],"synthesis,":[67],"by":[68,77,125,135],"Miyashita":[69],"co-workers":[71],"2004.":[73],"Our":[74],"studies":[75],"began":[76],"targeting":[78],"zoanthenol,":[79,120],"a":[80,205,213,219,222,254],"similar":[82],"natural":[83],"product":[84],"that":[85,242],"possesses":[86],"key":[88,275],"stereochemical":[89,128,270],"challenges":[90],"norzoanthamine,":[92],"while":[93],"offering":[94],"unique":[95],"opportunities":[96],"strategic":[98],"development":[99],"as":[100],"compared":[101],"other":[104],"members.":[106],"work":[109],"described":[110],"herein":[111],"focuses":[112],"on":[113],"approaches":[114],"tricyclic":[117],"core":[118],"specifically":[121],"employing":[122],"an":[123,157,192],"approach":[124],"which":[126],"complexity":[129],"C":[132,150],"ring,":[133],"marked":[134],"challenging":[137],"vicinal":[138],"all-carbon":[139],"quaternary":[140],"centers,":[141],"addressed":[143],"early":[144],"synthesis.":[147],"These":[148],"functionalized":[149],"ring":[151,160,172,201,230],"synthons":[152],"then":[154,217],"tethered":[155],"aromatic":[158],"A":[159,200],"synthon,":[161],"methods":[163],"form":[165],"final":[167],"bond":[168],"B":[171,229],"explored.":[174],"Special":[175],"given":[178],"acid-mediated":[181,189],"Friedel-Crafts":[182],"cyclization":[183,190,194],"approach.":[184],"In":[185,248],"addition":[186],"approach,":[191],"alternative":[193],"method":[195],"discussed":[197,273],"wherein":[198],"substituted":[203,224],"halogen":[206],"order":[208],"enable":[210],"generation":[211],"radical.":[214],"This":[215],"radical":[216],"undergoes":[218],"1,4-addition":[220],"into":[221],"fully":[223],"enone":[225],"close":[227],"provide":[232],"desired":[234],"stereochemistry":[235],"both":[236],"new":[240],"stereocenters":[241],"generated":[244],"cyclization.":[247],"efforts,":[250],"we":[251],"learned":[253],"great":[255],"deal":[256],"about":[257],"factors":[259],"governing":[260],"selectivity":[261],"reactivity":[263],"systems.":[266],"For":[267],"each":[268],"case,":[269],"models":[271],"structural":[276],"requirements":[277],"future":[279],"investigations":[280],"outlined.":[282]},"counts_by_year":[],"updated_date":"2026-10-12T09:40:04.860316","created_date":"2016-06-24T00:00:00"}