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Total Synthesis of (+)‐MPC1001B
Author(s) -
Kurogi Taichi,
Okaya Shun,
Fujiwara Hideto,
Okano Kentaro,
Tokuyama Hidetoshi
Publication year - 2016
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201507830
Subject(s) - intramolecular force , aldol reaction , chemistry , total synthesis , ring (chemistry) , fluoride , stereochemistry , organic chemistry , catalysis , inorganic chemistry
The first total synthesis of an epidithiodiketopiperazine alkaloid, (+)‐MPC1001B, was accomplished. This synthesis features a tetra‐ n ‐butylammonium fluoride mediated intramolecular aldol reaction for forming the 15‐membered macrolactone ring, and the construction of an epidithiodiketopiperazine substructure through a stepwise sulfenylation reaction involving a novel trityl trisulfide (TrSSS)‐group transfer.