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Enantioselective Total Synthesis of (−)‐Terengganensine A
Author(s) -
Piemontesi Cyril,
Wang Qian,
Zhu Jieping
Publication year - 2016
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201602374
Subject(s) - enantioselective synthesis , stereocenter , chemistry , iminium , stereochemistry , total synthesis , transfer hydrogenation , organic chemistry , catalysis , ruthenium
A seven‐step enantioselective total synthesis of (−)‐terengganensine A, a complex heptacyclic monoterpene indole alkaloid, was accomplished. Key steps included: a) Noyori's catalytic enantioselective transfer hydrogenation of the iminium salt to set up the absolute configuration at the C21 position; b) a highly diastereoselective C7 benzoyloxylation with dibenzoyl peroxide under mild conditions; and c) an integrated one‐pot oxidative cleavage of cyclopentene/triple cyclization/hydrolysis sequence for the construction of the dioxa azaadamantane motif with complete control of four newly generated stereocenters.