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Total Synthesis, Stereochemical Reassignment, and Biological Evaluation of (−)‐Lyngbyaloside B
Author(s) -
Fuwa Haruhiko,
Okuaki Yuta,
Yamagata Naoya,
Sasaki Makoto
Publication year - 2015
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201409629
Subject(s) - aldol reaction , ketene , chemistry , stereochemistry , aldol condensation , total synthesis , organic chemistry , catalysis
(−)‐Lyngbyaloside B is a 14‐membered macrolide glycoside isolated from the marine cyanobacterium Lyngbya sp. as a cytotoxic substance by Moore and co‐workers. The first total synthesis of (−)‐lyngbyaloside B and the reassignment of its stereostructure is described. The synthesis features an Abiko–Masamune aldol reaction, a vinylogous Mukaiyama aldol reaction, and a macrocyclization involving an acyl ketene intermediate for the construction of the macrocyclic backbone, which contains an acylated tertiary alcohol. The antiproliferative activity of selected compounds against a small panel of human cancer cell lines is also reported.