Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 55, Issue 22, Pages 6556-6560Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201602374
Keywords
asymmetric synthesis; domino cyclization; hydroxylation; monoterpene indole alkaloids; total synthesis
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Funding
- EPFL (Switzerland)
- Swiss National Science Foundation (SNSF)
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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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