Synthesis of (-)-lentiginosine, its 8a-epimer and dihydroxylated pyrrolizidine alkaloid from D-glucose

Chaudhari, Vinod D. ; Ajish Kumar, K. S. ; Dhavale, Dilip D. (2006) Synthesis of (-)-lentiginosine, its 8a-epimer and dihydroxylated pyrrolizidine alkaloid from D-glucose Tetrahedron, 62 (18). pp. 4349-4354. ISSN 0040-4020

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Official URL: http://linkinghub.elsevier.com/retrieve/pii/S00404...

Related URL: http://dx.doi.org/10.1016/j.tet.2006.02.074

Abstract

The D-glucose derived α,β-unsaturated ester 5 on 1,2-acetonide deprotection; oxidative diol cleavage followed by treatment with N-benzylamine in the presence of NaBH3CN undergoes reductive amination; a concomitant intramolecular conjugate addition reaction leading to the formation of dihydroxypyrrolidine-ester 6a; monohydroxypyrrolidine-γ-lactone 6b. Intermediates 6a and 6b were efficiently converted to (−)-lentiginosine 3a, its 8a-epimer 3b, pyrrolizidine azasugar 4 in good overall yield.

Item Type:Article
Source:Copyright of this article belongs to Elsevier Science.
Keywords:Alkaloids; Wittig Olefination; Azasugars
ID Code:9485
Deposited On:02 Nov 2010 12:07
Last Modified:31 May 2011 11:53

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