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Concise and Efficient Total Syntheses of Alkannin and Shikonin
Author(s) -
Nicolaou K. C.,
Hepworth David
Publication year - 1998
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/(sici)1521-3773(19980403)37:6<839::aid-anie839>3.0.co;2-j
Subject(s) - ketone , stereoselectivity , total synthesis , chemistry , organic chemistry , stereochemistry , combinatorial chemistry , catalysis
Two enantiomic natural products with wound‐healing properties , alkannin ( 1 ) and shikonin ( 2 ), are accessible by a short and efficient total synthesis. The success was achieved by a novel protecting system for masking of 5,8‐dihydroxy‐1,4‐naphthoquinones (naphthazarins) and a highly stereoselective ketone reduction.