Asymmetric Total Synthesis of (+)-Bermudenynol, a C-15 Laurencia Metabolite with a Vinyl Chloride Containing Oxocene Skeleton, through Intramolecular Amide Enolate Alkylation

A substrate-controlled asymmetric total synthesis of (+)-bermudenynol, a compact and synthetically challenging C(15)Laurencia metabolite that contains several halogen atoms, is reported. The oxocene core, which contains a vinyl chloride, was constructed by an efficient and highly stereoselective int...

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Published inAngewandte Chemie International Edition Vol. 53; no. 1; pp. 272 - 276
Main Authors Kim, Gyudong, Sohn, Te-Ik, Kim, Deukjoon, Paton, Robert S.
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 03.01.2014
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
ACETYLENIC ESTERS
PROTECTION
CONVERSION
oxocenes
EPOXIDATION
SECONDARY ALCOHOLS
STANNYLCUPRATION
AGENT
natural products
ETHERS
RING-CLOSING METATHESIS
intramolecular amide enolate alkylation
total synthesis
STEREOCONTROLLED SYNTHESIS
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Summary:A substrate-controlled asymmetric total synthesis of (+)-bermudenynol, a compact and synthetically challenging C(15)Laurencia metabolite that contains several halogen atoms, is reported. The oxocene core, which contains a vinyl chloride, was constructed by an efficient and highly stereoselective intramolecular amide enolate alkylation (IAEA). This result showcases the broad utility of the IAEA methodology as a useful alternative for cases in which the ring-closing metathesis is inefficient.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201308077