Highly diastereoselective hetero-Diels-Alder reaction of buta-1,3-diene with N-glyoxyloyl-(2R)-bornane-10,2-sultam:: an efficient synthesis of homochiral (S)-3-[2-{(methylsulfonyl)oxy}ethoxy]-4-(triphenylmethoxy)-1-butanol methanesulfonate

被引：8

作者：

Kosior, M

Malinowska, M

Józwik, J

Caille, JC

Jurczak, J

机构：

[1] Univ Warsaw, Dept Chem, PL-02093 Warsaw, Poland

[2] PPG SIPSY, F-49242 Avrille, France

[3] Polish Acad Sci, Inst Organ Chem, PL-01224 Warsaw, Poland

来源：

TETRAHEDRON-ASYMMETRY | 2003年 / 14卷 / 02期

关键词：

D O I：

10.1016/S0957-4166(02)00746-2

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The influence of Lewis acid on the diastereo selectivity of [4+2] cycloaddition of buta-1,3-diene to N-glyoxyloyl-(2R)-bornane-10,2-sultam was investigated and high levels of asymmetric induction were achieved. (S)-3-[2- (Methylsulfonyl)oxy}ethoxyl-4-(triphenylmethoxy)-1-butanol methanesulfonate were synthesized in 15% overall yield, applying as a crucial step the above-mentioned [4+2] cycloaddition catalyzed by ZnBr2. (C) 2003 Elsevier Science Ltd. All rights reserved.

引用

页码：239 / 244

页数：6

共 6 条

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[2] The asymmetric cyclocondensation reaction of 1-methoxy-3-silyloxybuta-1,3-dienes with N-glyoxyloyl-(2R)-bornane-10,2-sultam
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Jezewski, A
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[3] Stereochemical course of the [4+2] cycloaddition of 1-methoxybuta-1,3-diene to N-glyoxyloyl-(2R)-bornane-10,2-sultam. The formal synthesis of compactin and mevinolin
Bauer, T
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Jezewski, A
Kozak, J
Jurczak, J
TETRAHEDRON-ASYMMETRY, 1996, 7 (05) : 1391 - 1404
[4] Diastereoselective allylation of N-glyoxyloyl-(2R)-bornane-10,2-sultam and (1R)-8-phenylmenthyl glyoxylate:: synthesis of (2S,4S)-2-hydroxy-4-hydroxymethyl-4-butanolide
Kiegiel, K
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Jurczak, J
TETRAHEDRON-ASYMMETRY, 2004, 15 (24) : 3869 - 3878
[5] Hetero Diels-Aider-biocatalysis approach for the synthesis of (S)-3-[2-{(methylsulfonyl) oxy}ethoxy]-4-(triphenylmethoxy)-1-butanol methanesulfonate, a key intermediate for the synthesis of the PKC inhibitor LY333531
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Govindan, CK
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Yao, YM
ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2002, 6 (04) : 471 - 476
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STOODLEY, RJ
TETRAHEDRON LETTERS, 1994, 35 (34) : 6351 - 6354

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