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 | Zendy

Matsushima Yoshitaka | Zendy; Kino Jun | Zendy

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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.

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