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Enantioselective Total Synthesis of Chondrosterins I and J by Catalytic Asymmetric Intramolecular Aldol Reaction Using Chiral Diamine Catalyst
Author(s) -
Kawamoto Yuichiro,
Ozone Daiki,
Kobayashi Toyoharu,
Ito Hisanaka
Publication year - 2020
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202000579
Subject(s) - enantioselective synthesis , desymmetrization , chemistry , aldol reaction , ketone , diamine , intramolecular force , stereoselectivity , enantiomeric excess , catalysis , enantiomer , moiety , organocatalysis , organic chemistry , nitroaldol reaction , stereochemistry
The first enantioselective total synthesis of chondrosterins I and J was accomplished. The synthetic method focuses on an intramolecular aldol reaction through catalytic asymmetric desymmetrization using chiral diamine catalyst. An intensive investigation of this reaction improved the enantiomeric excess up to 92 % ee . In addition, stereoselective reduction of the ketone moiety efficiently converted chondrosterin I to chondrosterin J.