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Synthetic progress toward the marine natural product zamamiphidin A.


ABSTRACT: An asymmetric synthetic approach to the octahydrofuro[3,4-b]pyridine framework of marine natural product zamamiphidin A has been described. The key steps include an asymmetric Michael addition of (R)-N-tert-butanesulfinyl imidate with enamidomalonate to install the C10 stereocenter, an intramolecular alkoxide exchange/Michael addition/hydrogenation sequence to construct the bicyclic ring system.

SUBMITTER: Wang H 

PROVIDER: S-EPMC9050630 | biostudies-literature | 2020 Mar

REPOSITORIES: biostudies-literature

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Synthetic progress toward the marine natural product zamamiphidin A.

Wang Hao H   Tian Di D   Meng Zhaoxiang Z   Chen Zhihao Z   Xue Fei F   Liu Xiao-Yu XY   Song Hao H   Qin Yong Y  

RSC advances 20200324 20


An asymmetric synthetic approach to the octahydrofuro[3,4-<i>b</i>]pyridine framework of marine natural product zamamiphidin A has been described. The key steps include an asymmetric Michael addition of (<i>R</i>)-<i>N-tert</i>-butanesulfinyl imidate with enamidomalonate to install the C10 stereocenter, an intramolecular alkoxide exchange/Michael addition/hydrogenation sequence to construct the bicyclic ring system. ...[more]

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