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Total Syntheses of Lycoposerramine‐V and 5‐ epi ‐Lycoposerramine‐V
Author(s) -
Zhang LanDe,
Zhou TingTing,
Qi SenXing,
Xi Jie,
Yang XiaoLiang,
Yao ZhuJun
Publication year - 2014
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201402614
Subject(s) - cyclohexanone , desymmetrization , enantioselective synthesis , total synthesis , chemistry , stereoselectivity , amide , stereochemistry , intramolecular force , organic chemistry , catalysis
Enantioselective total syntheses of lycopodium alkaloids lycoposerramine‐V and 5‐ epi ‐lycoposerramine‐V have been accomplished. Features of the newly established total synthesis include: 1) introduction of the first chiral center with a scalable desymmetrization reaction of an meso ‐anhydride; 2) chemoselective functionalization of a bis‐Weinreb‐amide with Grignard addition; and 3) construction of the multifunctionalized cyclohexanone with a stereoselective intramolecular Michael addition.