Novel synthesis of castanospermine and 1-epicastanospermine

Linda Cronin; Paul V. Murphy

doi:10.1021/ol0508577

Novel synthesis of castanospermine and 1-epicastanospermine

Linda Cronin, Paul V. Murphy

University College Dublin

Research output: Contribution to a Journal (Peer & Non Peer) › Article › peer-review

49 Citations (Scopus)

Abstract

(Chemical Equation Presented) Polyhydroxylated indolizidines have potential for treatment of HIV, hepatitis C and HSV infection, multiple sclerosis, angiogenesis, cancer, and diabetes. A new synthetic approach to the title compounds from a 5-C-methoxypyranosyl azide has been developed. The route incorporates the aldol reaction and a novel catalytic reductive amination cascade to generate the indolizidine ring.

Original language	English
Pages (from-to)	2691-2693
Number of pages	3
Journal	Organic Letters
Volume	7
Issue number	13
DOIs	https://doi.org/10.1021/ol0508577
Publication status	Published - 2005
Externally published	Yes

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10.1021/ol0508577

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title = "Novel synthesis of castanospermine and 1-epicastanospermine",

abstract = "(Chemical Equation Presented) Polyhydroxylated indolizidines have potential for treatment of HIV, hepatitis C and HSV infection, multiple sclerosis, angiogenesis, cancer, and diabetes. A new synthetic approach to the title compounds from a 5-C-methoxypyranosyl azide has been developed. The route incorporates the aldol reaction and a novel catalytic reductive amination cascade to generate the indolizidine ring.",

author = "Linda Cronin and Murphy, {Paul V.}",

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AU - Cronin, Linda

AU - Murphy, Paul V.

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N2 - (Chemical Equation Presented) Polyhydroxylated indolizidines have potential for treatment of HIV, hepatitis C and HSV infection, multiple sclerosis, angiogenesis, cancer, and diabetes. A new synthetic approach to the title compounds from a 5-C-methoxypyranosyl azide has been developed. The route incorporates the aldol reaction and a novel catalytic reductive amination cascade to generate the indolizidine ring.

AB - (Chemical Equation Presented) Polyhydroxylated indolizidines have potential for treatment of HIV, hepatitis C and HSV infection, multiple sclerosis, angiogenesis, cancer, and diabetes. A new synthetic approach to the title compounds from a 5-C-methoxypyranosyl azide has been developed. The route incorporates the aldol reaction and a novel catalytic reductive amination cascade to generate the indolizidine ring.

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U2 - 10.1021/ol0508577

DO - 10.1021/ol0508577

M3 - Article

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SP - 2691

EP - 2693

JO - Organic Letters

JF - Organic Letters

IS - 13

ER -

Novel synthesis of castanospermine and 1-epicastanospermine

Abstract

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