The preparation of simplified scyphostatin analogues using a tethered aminohydroxylation (TA) strategy

M N  Kenworthy; G D  McAllister; R J K  Taylor

doi:10.1016/j.tetlet.2004.07.012

The preparation of simplified scyphostatin analogues using a tethered aminohydroxylation (TA) strategy

M N Kenworthy, G D McAllister, R J K Taylor

Chemistry

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

Abstract

The first tethered aminohydroxylation reaction employing a tertiary alcohol is reported as part of a route to prepare analogues of the naturally occurring sphingomyelinase inhibitor, scyphostatin. The tethered aminohydroxylation of 1-allylcyclohexanol produces the beta-amino alcohol product, in protected form, with the required regiochemistry. Two approaches to the installation of the lipophilic side chain are described and the successful route used to prepare five novel scyphostatin analogues, one containing the natural lower side chain. (C) 2004 Elsevier Ltd. All rights reserved.

Original language	English
Pages (from-to)	6661-6664
Number of pages	4
Journal	Tetrahedron Letters
Volume	45
Issue number	35
DOIs	https://doi.org/10.1016/j.tetlet.2004.07.012
Publication status	Published - 23 Aug 2004

Keywords

scyphostatin analogues
tethered aminohydroxylation
sphingomyelinase inhibitors
SELECTIVE IRREVERSIBLE INHIBITOR
NEUTRAL SPHINGOMYELINASE
EFFICIENT SYNTHESIS
MODEL-COMPOUND
CORE

Access to Document

10.1016/j.tetlet.2004.07.012

Cite this

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title = "The preparation of simplified scyphostatin analogues using a tethered aminohydroxylation (TA) strategy",

abstract = "The first tethered aminohydroxylation reaction employing a tertiary alcohol is reported as part of a route to prepare analogues of the naturally occurring sphingomyelinase inhibitor, scyphostatin. The tethered aminohydroxylation of 1-allylcyclohexanol produces the beta-amino alcohol product, in protected form, with the required regiochemistry. Two approaches to the installation of the lipophilic side chain are described and the successful route used to prepare five novel scyphostatin analogues, one containing the natural lower side chain. (C) 2004 Elsevier Ltd. All rights reserved.",

keywords = "scyphostatin analogues, tethered aminohydroxylation, sphingomyelinase inhibitors, SELECTIVE IRREVERSIBLE INHIBITOR, NEUTRAL SPHINGOMYELINASE, EFFICIENT SYNTHESIS, MODEL-COMPOUND, CORE",

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

year = "2004",

month = aug,

day = "23",

doi = "10.1016/j.tetlet.2004.07.012",

language = "English",

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pages = "6661--6664",

journal = "Tetrahedron Letters",

issn = "0040-4039",

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T1 - The preparation of simplified scyphostatin analogues using a tethered aminohydroxylation (TA) strategy

AU - Kenworthy, M N

AU - McAllister, G D

AU - Taylor, R J K

PY - 2004/8/23

Y1 - 2004/8/23

N2 - The first tethered aminohydroxylation reaction employing a tertiary alcohol is reported as part of a route to prepare analogues of the naturally occurring sphingomyelinase inhibitor, scyphostatin. The tethered aminohydroxylation of 1-allylcyclohexanol produces the beta-amino alcohol product, in protected form, with the required regiochemistry. Two approaches to the installation of the lipophilic side chain are described and the successful route used to prepare five novel scyphostatin analogues, one containing the natural lower side chain. (C) 2004 Elsevier Ltd. All rights reserved.

AB - The first tethered aminohydroxylation reaction employing a tertiary alcohol is reported as part of a route to prepare analogues of the naturally occurring sphingomyelinase inhibitor, scyphostatin. The tethered aminohydroxylation of 1-allylcyclohexanol produces the beta-amino alcohol product, in protected form, with the required regiochemistry. Two approaches to the installation of the lipophilic side chain are described and the successful route used to prepare five novel scyphostatin analogues, one containing the natural lower side chain. (C) 2004 Elsevier Ltd. All rights reserved.

KW - scyphostatin analogues

KW - tethered aminohydroxylation

KW - sphingomyelinase inhibitors

KW - SELECTIVE IRREVERSIBLE INHIBITOR

KW - NEUTRAL SPHINGOMYELINASE

KW - EFFICIENT SYNTHESIS

KW - MODEL-COMPOUND

KW - CORE

U2 - 10.1016/j.tetlet.2004.07.012

DO - 10.1016/j.tetlet.2004.07.012

M3 - Article

SN - 0040-4039

VL - 45

SP - 6661

EP - 6664

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 35

ER -