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research article
Enantioselective Total Synthesis of (−)-Terengganensine A
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.
Type
research article
Web of Science ID
WOS:000377921200036
Authors
Publication date
2016
Publisher
Published in
Volume
55
Issue
22
Start page
6556
End page
6560
Peer reviewed
REVIEWED
EPFL units
Available on Infoscience
May 20, 2016
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