An improved synthesis of the scyphostatin side-chain

G D  McAllister; R J K  Taylor

doi:10.1016/j.tetlet.2004.01.156

An improved synthesis of the scyphostatin side-chain

G D McAllister, R J K Taylor

Chemistry

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

Abstract

A formal synthesis of the lipophilic side-chain of scyphostatin has been achieved using a convergent synthesis, in 16% yield over,six steps. This synthesis involves enzymatic desymmetrisation of a meso-diol, resolution of 2-methylbutan-1-ol, stereoselective hydrozirconation of a volatile acetylene and a Negishi-style cross coupling. (C) 2004 Elsevier Ltd. All rights reserved.

Original language	English
Pages (from-to)	2551-2554
Number of pages	4
Journal	Tetrahedron Letters
Volume	45
Issue number	12
DOIs	https://doi.org/10.1016/j.tetlet.2004.01.156
Publication status	Published - 15 Mar 2004

Keywords

natural products
stereoselective synthesis
enzymes
desymmetrisation
cross-coupling
STEREOSELECTIVE SYNTHESIS
ASYMMETRIC-SYNTHESIS
MODEL-COMPOUND
SEX-PHEROMONE
CORE
CONFIGURATION
STEREOISOMERS
CONVERGENT

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10.1016/j.tetlet.2004.01.156

Cite this

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title = "An improved synthesis of the scyphostatin side-chain",

abstract = "A formal synthesis of the lipophilic side-chain of scyphostatin has been achieved using a convergent synthesis, in 16% yield over,six steps. This synthesis involves enzymatic desymmetrisation of a meso-diol, resolution of 2-methylbutan-1-ol, stereoselective hydrozirconation of a volatile acetylene and a Negishi-style cross coupling. (C) 2004 Elsevier Ltd. All rights reserved.",

keywords = "natural products, stereoselective synthesis, enzymes, desymmetrisation, cross-coupling, STEREOSELECTIVE SYNTHESIS, ASYMMETRIC-SYNTHESIS, MODEL-COMPOUND, SEX-PHEROMONE, CORE, CONFIGURATION, STEREOISOMERS, CONVERGENT",

author = "McAllister, {G D} and Taylor, {R J K}",

year = "2004",

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journal = "Tetrahedron Letters",

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T1 - An improved synthesis of the scyphostatin side-chain

AU - McAllister, G D

AU - Taylor, R J K

PY - 2004/3/15

Y1 - 2004/3/15

N2 - A formal synthesis of the lipophilic side-chain of scyphostatin has been achieved using a convergent synthesis, in 16% yield over,six steps. This synthesis involves enzymatic desymmetrisation of a meso-diol, resolution of 2-methylbutan-1-ol, stereoselective hydrozirconation of a volatile acetylene and a Negishi-style cross coupling. (C) 2004 Elsevier Ltd. All rights reserved.

AB - A formal synthesis of the lipophilic side-chain of scyphostatin has been achieved using a convergent synthesis, in 16% yield over,six steps. This synthesis involves enzymatic desymmetrisation of a meso-diol, resolution of 2-methylbutan-1-ol, stereoselective hydrozirconation of a volatile acetylene and a Negishi-style cross coupling. (C) 2004 Elsevier Ltd. All rights reserved.

KW - natural products

KW - stereoselective synthesis

KW - enzymes

KW - desymmetrisation

KW - cross-coupling

KW - STEREOSELECTIVE SYNTHESIS

KW - ASYMMETRIC-SYNTHESIS

KW - MODEL-COMPOUND

KW - SEX-PHEROMONE

KW - CORE

KW - CONFIGURATION

KW - STEREOISOMERS

KW - CONVERGENT

U2 - 10.1016/j.tetlet.2004.01.156

DO - 10.1016/j.tetlet.2004.01.156

M3 - Article

SN - 0040-4039

VL - 45

SP - 2551

EP - 2554

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 12

ER -