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Synthesis of (+)‐ trans ‐Dihydrolycoricidine by an Organocatalytic Enantioselective Friedel–Crafts Reaction
Author(s) -
Kato Masaru,
Yasui Koji,
Yamanaka Masahiro,
Nagasawa Kazuo
Publication year - 2016
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201500469
Subject(s) - chemistry , enantioselective synthesis , friedel–crafts reaction , ring (chemistry) , intramolecular force , amaryllidaceae alkaloids , olefin fiber , stereoselectivity , nitro , organocatalysis , total synthesis , sesamol , stereochemistry , catalysis , medicinal chemistry , organic chemistry , alkaloid , alkyl , antioxidant
The amaryllidaceae alkaloid (+)‐ trans ‐dihydrolycoricidine ( 1 ) was synthesized by asymmetric organocatalytic Friedel–Crafts reaction of sesamol with nitro‐olefin followed by an intramolecular Henry reaction for construction of the C ring system. Construction of the B ring was achieved by a microwave‐assisted palladium‐catalyzed CO insertion reaction. Finally, regio‐ and stereoselective introduction of the third hydroxyl group (at C3) on the C ring afforded 1 .
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