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Enantioselective Total Synthesis of (+)‐Neostenine
Author(s) -
Nakayama Yasuaki,
Maeda Yuichiro,
Kotatsu Masayuki,
Sekiya Ruriko,
Ichiki Masato,
Sato Takaaki,
Chida Noritaka
Publication year - 2016
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201600058
Subject(s) - enantioselective synthesis , stereocenter , moiety , total synthesis , allylic rearrangement , stereochemistry , chirality (physics) , diol , chemistry , claisen rearrangement , polyol , sequence (biology) , combinatorial chemistry , catalysis , organic chemistry , chiral symmetry , physics , biochemistry , nambu–jona lasinio model , quantum mechanics , quark , polyurethane
A chirality transfer approach using acyclic polyol intermediates for the synthesis of (+)‐neostenine ( 1 ) has been developed. The sequential Overman/Claisen rearrangement of an allylic 1,2‐diol was especially useful, installing two contiguous stereocenters with complete diastereoselectivity in a one‐pot sequence. The SmI 2 ‐mediated cyclization and the subsequent chemoselective reduction of a lactam moiety accomplished the first enantioselective total synthesis of (+)‐neostenine ( 1 ).
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