An efficient asymmetric synthesis of grenadamide

R Green; M Cheeseman; S Duffill; A Merritt; S D Bull

doi:10.1016/j.tetlet.2005.09.087

An efficient asymmetric synthesis of grenadamide

R Green, M Cheeseman, S Duffill, A Merritt, S D Bull

Department of Chemistry

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26 Citations (SciVal)

Abstract

The cyclopropane containing natural product grenadamide has been prepared in six steps using (R)-5,5-dimethyl-oxazolidin-2-one as a chiral auxiliary for asymmetric synthesis. Key synthetic steps include the use of the P-hydroxyl group of a syn-aldol product as a 'temporary' stereocentre to control the facial selectivity of a directed cyclopropanation reaction, as well as the use of phenylethylamine as a nucleophile for the direct aminolysis of an N-acyl-oxazolidin-2-one intermediate. (c) 2005 Elsevier Ltd. All rights reserved.

Original language	English
Pages (from-to)	7931-7934
Number of pages	4
Journal	Tetrahedron Letters
Volume	46
Issue number	46
DOIs	https://doi.org/10.1016/j.tetlet.2005.09.087
Publication status	Published - 2005

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ID number: ISI:000232860300016

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10.1016/j.tetlet.2005.09.087

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title = "An efficient asymmetric synthesis of grenadamide",

abstract = "The cyclopropane containing natural product grenadamide has been prepared in six steps using (R)-5,5-dimethyl-oxazolidin-2-one as a chiral auxiliary for asymmetric synthesis. Key synthetic steps include the use of the P-hydroxyl group of a syn-aldol product as a 'temporary' stereocentre to control the facial selectivity of a directed cyclopropanation reaction, as well as the use of phenylethylamine as a nucleophile for the direct aminolysis of an N-acyl-oxazolidin-2-one intermediate. (c) 2005 Elsevier Ltd. All rights reserved.",

author = "R Green and M Cheeseman and S Duffill and A Merritt and Bull, \{S D\}",

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T1 - An efficient asymmetric synthesis of grenadamide

AU - Green, R

AU - Cheeseman, M

AU - Duffill, S

AU - Merritt, A

AU - Bull, S D

N1 - ID number: ISI:000232860300016

PY - 2005

Y1 - 2005

N2 - The cyclopropane containing natural product grenadamide has been prepared in six steps using (R)-5,5-dimethyl-oxazolidin-2-one as a chiral auxiliary for asymmetric synthesis. Key synthetic steps include the use of the P-hydroxyl group of a syn-aldol product as a 'temporary' stereocentre to control the facial selectivity of a directed cyclopropanation reaction, as well as the use of phenylethylamine as a nucleophile for the direct aminolysis of an N-acyl-oxazolidin-2-one intermediate. (c) 2005 Elsevier Ltd. All rights reserved.

AB - The cyclopropane containing natural product grenadamide has been prepared in six steps using (R)-5,5-dimethyl-oxazolidin-2-one as a chiral auxiliary for asymmetric synthesis. Key synthetic steps include the use of the P-hydroxyl group of a syn-aldol product as a 'temporary' stereocentre to control the facial selectivity of a directed cyclopropanation reaction, as well as the use of phenylethylamine as a nucleophile for the direct aminolysis of an N-acyl-oxazolidin-2-one intermediate. (c) 2005 Elsevier Ltd. All rights reserved.

U2 - 10.1016/j.tetlet.2005.09.087

DO - 10.1016/j.tetlet.2005.09.087

M3 - Article

SN - 0040-4039

VL - 46

SP - 7931

EP - 7934

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 46

ER -

An efficient asymmetric synthesis of grenadamide

Abstract

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