Total Synthesis of (−)‐Ophiodilactone A and (−)‐Ophiodilactone B | Zendy

Matsubara Takaaki | Zendy; Takahashi Keisuke | Zendy; Ishihara Jun | Zendy; Hatakeyama Susumi | Zendy

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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 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.201307835

Subject(s) - lactone , epoxide , total synthesis , intramolecular force , chemistry , 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.

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