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A Stereoselective Approach toward (−)-Lepadins A–C

Author:
Li, Xiong, Hu, Lingling, Jia, Junhao, Gu, He, Jia, Yuanliang, Chen, Xiaochuan
Source:
Organic letters 2017 v.19 no.19 pp. 5372-5375
ISSN:
1523-7052
Subject:
chemical structure, cycloaddition reactions, organic compounds, stereoselectivity
Abstract:
A new short approach to (−)-lepadins A–C has been developed based on a stereocontrolled Diels–Alder reaction employing a chiral dienophile. With this approach, (−)-lepadin B is synthesized from 5-deoxy-d-ribose in 13 steps with 14.8% overall yield. The cis-decahydroquinoline core containing five stereocenters could be rapidly constructed via stereoselective cycloaddition and subsequent five-step one-pot hydrogenation–cyclization.
Agid:
5827006