Stereoselective reactions of a (-)-quinic acid-derived enone: Application to the synthesis of the core of scyphostatin

L M  Murray; Peter Andrew O'Brien; R J K  Taylor

doi:10.1021/ol034521d

Stereoselective reactions of a (-)-quinic acid-derived enone: Application to the synthesis of the core of scyphostatin

L M Murray, Peter Andrew O'Brien, R J K Taylor

Chemistry

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

Abstract

[GRAPHIC]

A (-)-quinic acid-derived enone, with the trans-1,2-diol protected as a 2,3-dimethoxybutanediyldioxy ketal, provides an excellent template for further highly stereoselective elaboration as exemplified by its conversion into the core of scyphostatin, a potent inhibitor of neutral sphingomyelinase.

Original language	English
Pages (from-to)	1943-1946
Number of pages	4
Journal	Organic Letters
Volume	5
Issue number	11
DOIs	https://doi.org/10.1021/ol034521d
Publication status	Published - 29 May 2003

Keywords

BOND FORMING REACTIONS
PI-FACIAL SELECTIVITY
LITHIUM AMIDE BASES
ASYMMETRIC-SYNTHESIS
MODEL-COMPOUND
4-DEOXYCONDURITOLS
DEPROTONATION
CONFIGURATION
BEARING

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10.1021/ol034521d

Cite this

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title = "Stereoselective reactions of a (-)-quinic acid-derived enone: Application to the synthesis of the core of scyphostatin",

abstract = "[GRAPHIC]A (-)-quinic acid-derived enone, with the trans-1,2-diol protected as a 2,3-dimethoxybutanediyldioxy ketal, provides an excellent template for further highly stereoselective elaboration as exemplified by its conversion into the core of scyphostatin, a potent inhibitor of neutral sphingomyelinase.",

keywords = "BOND FORMING REACTIONS, PI-FACIAL SELECTIVITY, LITHIUM AMIDE BASES, ASYMMETRIC-SYNTHESIS, MODEL-COMPOUND, 4-DEOXYCONDURITOLS, DEPROTONATION, CONFIGURATION, BEARING",

author = "Murray, {L M} and O'Brien, {Peter Andrew} and Taylor, {R J K}",

year = "2003",

month = may,

day = "29",

doi = "10.1021/ol034521d",

language = "English",

volume = "5",

pages = "1943--1946",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "11",

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TY - JOUR

T1 - Stereoselective reactions of a (-)-quinic acid-derived enone: Application to the synthesis of the core of scyphostatin

AU - Murray, L M

AU - O'Brien, Peter Andrew

AU - Taylor, R J K

PY - 2003/5/29

Y1 - 2003/5/29

N2 - [GRAPHIC]A (-)-quinic acid-derived enone, with the trans-1,2-diol protected as a 2,3-dimethoxybutanediyldioxy ketal, provides an excellent template for further highly stereoselective elaboration as exemplified by its conversion into the core of scyphostatin, a potent inhibitor of neutral sphingomyelinase.

AB - [GRAPHIC]A (-)-quinic acid-derived enone, with the trans-1,2-diol protected as a 2,3-dimethoxybutanediyldioxy ketal, provides an excellent template for further highly stereoselective elaboration as exemplified by its conversion into the core of scyphostatin, a potent inhibitor of neutral sphingomyelinase.

KW - BOND FORMING REACTIONS

KW - PI-FACIAL SELECTIVITY

KW - LITHIUM AMIDE BASES

KW - ASYMMETRIC-SYNTHESIS

KW - MODEL-COMPOUND

KW - 4-DEOXYCONDURITOLS

KW - DEPROTONATION

KW - CONFIGURATION

KW - BEARING

U2 - 10.1021/ol034521d

DO - 10.1021/ol034521d

M3 - Article

SN - 1523-7060

VL - 5

SP - 1943

EP - 1946

JO - Organic Letters

JF - Organic Letters

IS - 11

ER -