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

Vinod D. Chaudhari; K. S. Ajish Kumar; Dilip D. Dhavale

doi:10.1016/j.tet.2006.02.074

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

Vinod D. Chaudhari, K. S. Ajish Kumar, Dilip D. Dhavale

Research output: Contribution to journal › Article › peer-review

31 Scopus citations

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 and a concomitant intramolecular conjugate addition reaction leading to the formation of dihydroxypyrrolidine-ester 6a and monohydroxypyrrolidine-γ-lactone 6b. Intermediates 6a and 6b were efficiently converted to (-)-lentiginosine 3a, its 8a-epimer 3b, and pyrrolizidine azasugar 4 in good overall yield.

Original language	English
Pages (from-to)	4349-4354
Number of pages	6
Journal	Tetrahedron
Volume	62
Issue number	18
DOIs	https://doi.org/10.1016/j.tet.2006.02.074
State	Published - 1 May 2006
Externally published	Yes

Keywords

Alkaloids
Azasugars
Wittig olefination

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tet.2006.02.074

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title = "Synthesis of (-)-lentiginosine, its 8a-epimer and dihydroxylated pyrrolizidine alkaloid from d-glucose",

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 and a concomitant intramolecular conjugate addition reaction leading to the formation of dihydroxypyrrolidine-ester 6a and monohydroxypyrrolidine-γ-lactone 6b. Intermediates 6a and 6b were efficiently converted to (-)-lentiginosine 3a, its 8a-epimer 3b, and pyrrolizidine azasugar 4 in good overall yield.",

keywords = "Alkaloids, Azasugars, Wittig olefination",

author = "Chaudhari, {Vinod D.} and {Ajish Kumar}, {K. S.} and Dhavale, {Dilip D.}",

year = "2006",

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T1 - Synthesis of (-)-lentiginosine, its 8a-epimer and dihydroxylated pyrrolizidine alkaloid from d-glucose

AU - Chaudhari, Vinod D.

AU - Ajish Kumar, K. S.

AU - Dhavale, Dilip D.

PY - 2006/5/1

Y1 - 2006/5/1

N2 - 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 and a concomitant intramolecular conjugate addition reaction leading to the formation of dihydroxypyrrolidine-ester 6a and monohydroxypyrrolidine-γ-lactone 6b. Intermediates 6a and 6b were efficiently converted to (-)-lentiginosine 3a, its 8a-epimer 3b, and pyrrolizidine azasugar 4 in good overall yield.

AB - 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 and a concomitant intramolecular conjugate addition reaction leading to the formation of dihydroxypyrrolidine-ester 6a and monohydroxypyrrolidine-γ-lactone 6b. Intermediates 6a and 6b were efficiently converted to (-)-lentiginosine 3a, its 8a-epimer 3b, and pyrrolizidine azasugar 4 in good overall yield.

KW - Alkaloids

KW - Azasugars

KW - Wittig olefination

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DO - 10.1016/j.tet.2006.02.074

M3 - Article

AN - SCOPUS:33646106115

SN - 0040-4020

VL - 62

SP - 4349

EP - 4354

JO - Tetrahedron

JF - Tetrahedron

IS - 18

ER -

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

Abstract

Keywords

ASJC Scopus subject areas

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