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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 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.201507830
Subject(s) - intramolecular force , aldol reaction , total synthesis , ring (chemistry) , chemistry , stereochemistry , substructure , fluoride , organic chemistry , catalysis , engineering , inorganic chemistry , structural engineering
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.
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