Improved Synthesis of Epothilone B Employing Alkylation of an Alkyne for Assembly of Subunits

A strategy for assembling the two principal modules of epothilone B was developed that merges an allylic bromide with a terminal acetylene to fabricate the C10−C11 bond of the macrocycle. The resulting alkyne was semihydrogenated to give a seco ester previously employed in our total synthesis of epo...

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Veröffentlicht in:	Organic letters 1999-11, Vol.1 (9), p.1431-1434
Hauptverfasser:	White, James D, Sundermann, Kurt F, Carter, Rich G
Format:	Artikel
Sprache:	eng
Schlagworte:	Alkylation Alkynes - chemistry Antineoplastic Agents - chemical synthesis Antineoplastic Agents - chemistry Epothilones Epoxy Compounds - chemical synthesis Epoxy Compounds - chemistry Thiazoles - chemical synthesis Thiazoles - chemistry
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description	A strategy for assembling the two principal modules of epothilone B was developed that merges an allylic bromide with a terminal acetylene to fabricate the C10−C11 bond of the macrocycle. The resulting alkyne was semihydrogenated to give a seco ester previously employed in our total synthesis of epothilone B. This new approach affords a more efficient route to the naturally occurring macrolide and to its 9,10-dehydro analogue.
doi_str_mv	10.1021/ol990248x
format	Article
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Lett</addtitle><description>A strategy for assembling the two principal modules of epothilone B was developed that merges an allylic bromide with a terminal acetylene to fabricate the C10−C11 bond of the macrocycle. The resulting alkyne was semihydrogenated to give a seco ester previously employed in our total synthesis of epothilone B. This new approach affords a more efficient route to the naturally occurring macrolide and to its 9,10-dehydro analogue.</description><subject>Alkylation</subject><subject>Alkynes - chemistry</subject><subject>Antineoplastic Agents - chemical synthesis</subject><subject>Antineoplastic Agents - chemistry</subject><subject>Epothilones</subject><subject>Epoxy Compounds - chemical synthesis</subject><subject>Epoxy Compounds - chemistry</subject><subject>Thiazoles - chemical synthesis</subject><subject>Thiazoles - chemistry</subject><issn>1523-7060</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1999</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkMtOwzAQRS0EoqWw4AdQNiCxCPiRh70sVXlIlVi0WxQ5yZimOHaJE0T-HpdUFQsWoxndObqauQhdEnxHMCX3VguBacS_j9CYxJSFKY7p8WFO8AidObfBmHhFnKIRwZzGgosxenupt439gjJY9qZdg6tcYFUw39p2XWlrIHgI5vVW274y78FUf_RatpU1O0iaX8EzyjbB1Dmoc93vNssu70zVunN0oqR2cLHvE7R6nK9mz-Hi9ellNl2EkhHShjQvU0EkU9wXlbRQRVxGqgBeCBynVPhzc2ApAS4hSaAExZM0Ag6cMYHZBN0Mtv6Vzw5cm9WVK0BracB2LktExHHMYg_eDmDRWOcaUNm2qWrZ9BnB2S7K7BClZ6_2pl1eQ_mHHLLzwPUAyMJlG9s1xr_4j9EP9pF7qg</recordid><startdate>19991104</startdate><enddate>19991104</enddate><creator>White, James D</creator><creator>Sundermann, Kurt F</creator><creator>Carter, Rich G</creator><general>American Chemical Society</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>19991104</creationdate><title>Improved Synthesis of Epothilone B Employing Alkylation of an Alkyne for Assembly of Subunits</title><author>White, James D ; Sundermann, Kurt F ; Carter, Rich G</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a311t-2bd791a3f8a3f2a2cfc5d4fce8c905729082be371e8ae66edef8674e8e833903</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1999</creationdate><topic>Alkylation</topic><topic>Alkynes - chemistry</topic><topic>Antineoplastic Agents - chemical synthesis</topic><topic>Antineoplastic Agents - chemistry</topic><topic>Epothilones</topic><topic>Epoxy Compounds - chemical synthesis</topic><topic>Epoxy Compounds - chemistry</topic><topic>Thiazoles - chemical synthesis</topic><topic>Thiazoles - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>White, James D</creatorcontrib><creatorcontrib>Sundermann, Kurt F</creatorcontrib><creatorcontrib>Carter, Rich G</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Organic letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>White, James D</au><au>Sundermann, Kurt F</au><au>Carter, Rich G</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Improved Synthesis of Epothilone B Employing Alkylation of an Alkyne for Assembly of Subunits</atitle><jtitle>Organic letters</jtitle><addtitle>Org. 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subjects	Alkylation Alkynes - chemistry Antineoplastic Agents - chemical synthesis Antineoplastic Agents - chemistry Epothilones Epoxy Compounds - chemical synthesis Epoxy Compounds - chemistry Thiazoles - chemical synthesis Thiazoles - chemistry
title	Improved Synthesis of Epothilone B Employing Alkylation of an Alkyne for Assembly of Subunits
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