Enzymatic kinetic resolution of primary allenic alcohols. Application to the total synthesis and stereochemical assignment of striatisporolide A

Jan Deska; Jan-E. Bäckvall

doi:10.1039/B912128P

Enzymatic kinetic resolution of primary allenic alcohols. Application to the total synthesis and stereochemical assignment of striatisporolide A

Jan Deska, Jan-E. Bäckvall

Not published at Aalto University

Stockholm University

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

Abstract

Crude porcine pancreatic lipase was successfully used for the kinetic resolution of axially chiral primary allenic alcohols providing very high enantioselectivities with E values above 200. This simple access to optically active allenes was applied to the total synthesis of the fungal metabolite (−)-striatisporolide A, allowing its unambiguous stereochemical assignment.

Original language	English
Pages (from-to)	3379-3381
Number of pages	3
Journal	ORGANIC AND BIOMOLECULAR CHEMISTRY
Volume	7
DOIs	https://doi.org/10.1039/B912128P
Publication status	Published - 29 Jun 2009
MoE publication type	A1 Journal article-refereed

Keywords

natural product synthesis
chemoenzymatic
lipase
kinetic resolution
heterocycles
biocatalysis

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10.1039/B912128P

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title = "Enzymatic kinetic resolution of primary allenic alcohols. Application to the total synthesis and stereochemical assignment of striatisporolide A",

abstract = "Crude porcine pancreatic lipase was successfully used for the kinetic resolution of axially chiral primary allenic alcohols providing very high enantioselectivities with E values above 200. This simple access to optically active allenes was applied to the total synthesis of the fungal metabolite (−)-striatisporolide A, allowing its unambiguous stereochemical assignment.",

keywords = "natural product synthesis, chemoenzymatic, lipase, kinetic resolution, heterocycles, biocatalysis",

author = "Jan Deska and Jan-E. B{\"a}ckvall",

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AU - Deska, Jan

AU - Bäckvall, Jan-E.

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Y1 - 2009/6/29

N2 - Crude porcine pancreatic lipase was successfully used for the kinetic resolution of axially chiral primary allenic alcohols providing very high enantioselectivities with E values above 200. This simple access to optically active allenes was applied to the total synthesis of the fungal metabolite (−)-striatisporolide A, allowing its unambiguous stereochemical assignment.

AB - Crude porcine pancreatic lipase was successfully used for the kinetic resolution of axially chiral primary allenic alcohols providing very high enantioselectivities with E values above 200. This simple access to optically active allenes was applied to the total synthesis of the fungal metabolite (−)-striatisporolide A, allowing its unambiguous stereochemical assignment.

KW - natural product synthesis

KW - chemoenzymatic

KW - lipase

KW - kinetic resolution

KW - heterocycles

KW - biocatalysis

U2 - 10.1039/B912128P

DO - 10.1039/B912128P

M3 - Article

SN - 1477-0520

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JO - ORGANIC AND BIOMOLECULAR CHEMISTRY

JF - ORGANIC AND BIOMOLECULAR CHEMISTRY

ER -

Enzymatic kinetic resolution of primary allenic alcohols. Application to the total synthesis and stereochemical assignment of striatisporolide A

Abstract

Keywords

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