☆ 4.8 Article

Enantioselective Total Synthesis of (-)-Terengganensine A

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2016)

Journal

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Volume 55, Issue 22, Pages 6556-6560

Publisher

WILEY-V C H VERLAG GMBH

DOI: 10.1002/anie.201602374

Keywords

asymmetric synthesis; domino cyclization; hydroxylation; monoterpene indole alkaloids; total synthesis

Categories

Chemistry, Multidisciplinary

Funding

EPFL (Switzerland)
Swiss National Science Foundation (SNSF)

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Abstract

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.

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