Asymmetric Total Synthesis and Formal Total Synthesis of the Antitumor Sesquiterpenoid (+)-Eremantholide A

A new asymmetric total synthesis of (+)-eremantholide A is reported in which a Hoveyda−Grubbs ring-closing metathesis (RCM) reaction is used to assemble the nine-membered oxonin ring, and an enolate alkylation between the 3(2H)-furanone 2 and O-triflate 3 is exploited for C(9)−C(10) bond constructio...

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Bibliographic Details
Published inOrganic letters Vol. 9; no. 7; pp. 1267 - 1270
Main Authors Li, Yi, Hale, Karl J
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 29.03.2007
Amer Chemical Soc
Subjects
Alkylation
Antineoplastic Agents, Phytogenic - chemical synthesis
Antineoplastic Agents, Phytogenic - chemistry
Antineoplastic Agents, Phytogenic - pharmacology
Cell Line, Tumor
Cell Proliferation - drug effects
Chemistry
Chemistry, Organic
Cyclization
Humans
Molecular Structure
Oxidation-Reduction
Physical Sciences
Science & Technology
Sesquiterpenes - chemical synthesis
Sesquiterpenes - chemistry
Sesquiterpenes - pharmacology
Stereoisomerism
OXIDATION
ALCOHOLS
DEPROTONATION
ENANTIOSELECTIVE SYNTHESIS
LACTONES
METATHESIS
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Summary:A new asymmetric total synthesis of (+)-eremantholide A is reported in which a Hoveyda−Grubbs ring-closing metathesis (RCM) reaction is used to assemble the nine-membered oxonin ring, and an enolate alkylation between the 3(2H)-furanone 2 and O-triflate 3 is exploited for C(9)−C(10) bond construction. An Evans asymmetric aldol reaction and a Sharpless asymmetric epoxidation served to stereoselectively install the C(6), C(7), and C(8) stereocenters of the target structure.
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol0700862