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Synthesis of N ‐Bz‐Protected D ‐Daunosamine and D ‐Ristosamine by Silica Gel Promoted Intramolecular Conjugate Addition of Trichloroacetimidates obtained from Osmundalactone and Its Epimer
Author(s) -
Matsushima Yoshitaka,
Kino Jun
Publication year - 2010
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.200901402
Subject(s) - chemistry , intramolecular force , conjugate , epimer , silica gel , stereochemistry , organic chemistry , mathematical analysis , mathematics
Trichloroacetimidates prepared from osmundalactone and its epimer unexpectedly undergo intramolecular conjugate addition during silica gel chromatography to produce oxazolines in excellent yields. The novel, simple synthesis of N ‐Bz‐protected D ‐daunosamine and D ‐ristosamine from these oxazolines is described in this paper.