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Total Synthesis of (−)‐Ophiodilactone A and (−)‐Ophiodilactone B
Author(s) -
Matsubara Takaaki,
Takahashi Keisuke,
Ishihara Jun,
Hatakeyama Susumi
Publication year - 2014
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201307835
Subject(s) - total synthesis , epoxide , lactone , chemistry , intramolecular force , stereochemistry , enantioselective synthesis , organic chemistry , catalysis
The first asymmetric total synthesis of (−)‐ophiodilactone A and (−)‐ophiodilactone B, isolated from the ophiuroid (Ophiocoma scolopendrina), is reported. The key features of the synthesis include the highly stereocontrolled construction of the structurally congested γ‐lactone/δ‐lactone skeleton through an asymmetric epoxidation, diastereoselective iodolactonization, and intramolecular epoxide‐opening with a carboxylic acid, and biomimetic radical cyclization of ophiodilactone A to ophiodilactone B.