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Asymmetric Total Synthesis of (+)‐Bermudenynol, a C 15 Laurencia Metabolite with a Vinyl Chloride Containing Oxocene Skeleton, through Intramolecular Amide Enolate Alkylation
Author(s) -
Kim Gyudong,
Sohn Teik,
Kim Deukjoon,
Paton Robert S.
Publication year - 2014
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201308077
Subject(s) - intramolecular force , total synthesis , amide , chemistry , laurencia , alkylation , metabolite , ring closing metathesis , stereochemistry , metathesis , substrate (aquarium) , stereoselectivity , organic chemistry , biology , botany , polymerization , catalysis , ecology , biochemistry , polymer , algae
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.