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Total synthesis of (+)-trans- dihydronarciclasine from (+)-7-azabicyclo[2.2.1]heptanone

Author:
Pandey, Ganesh, Fernandes, Rushil, Dey, Debasis, Majumder, Binoy
Source:
Tetrahedron 2018 v.74 no.39 pp. 5752-5757
ISSN:
0040-4020
Subject:
Amaryllidaceae, alkaloids, chemical structure, cyclohexanes, olefin, oxidation, regioselectivity, stereoselectivity
Abstract:
A concise asymmetric total synthesis of Amaryllidaceae alkaloid (+)-trans-dihydronarciclasine is accomplished starting from optically pure 7-azabicyclo[2.2.1]heptanone scaffold in 13 linear steps. Key features of the strategy include substrate-directed stereoselective installation of the trans B-C ring junction and regioselective Wacker-type internal olefin oxidation to provide a rapid access to all hydroxyl functionalities over the key cyclohexane ring in a stereocontrolled manner.
Agid:
6114306