Asymmetric Total Synthesis of (−)-Lycospidine
A
Version 3 2016-09-12, 20:27
Version 2 2016-08-29, 15:50
Version 1 2016-08-26, 20:14
Posted on 2016-08-26 - 00:00
The first asymmetric
total synthesis of the structurally unique Lycopodium alkaloid (−)-lycospidine A, containing
an unprecedented five-membered ring, has been accomplished in only
10 steps with 21.6% overall yield from the known conveniently available
sulfoxide. This protecting-group-free short synthesis relied on the
use of a key amidation/aza-Prins domino cyclization reaction to rapidly
construct the tricyclic skeleton and two continuous stereocenters
(one of which is a bridged quaternary stereocenter). An intramolecular
aldol condensation was successfully utilized to establish the unique
five-membered ring, and a late-stage oxidation inspired by biosynthesis
pathway was adopted to synthesize the diosphenol ring of (−)-lycospidine
A.
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Xu, Shiyan; Zhang, Jing; Ma, Donghui; Xu, Dengyu; Xie, Xingang; She, Xuegong (2016). Asymmetric Total Synthesis of (−)-Lycospidine
A. ACS Publications. Collection. https://doi.org/10.1021/acs.orglett.6b02322
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AUTHORS (6)
SX
Shiyan Xu
JZ
Jing Zhang
DM
Donghui Ma
DX
Dengyu Xu
XX
Xingang Xie
XS
Xuegong She