Synthesis of a 'twisted' transition-state analogue of biotin

被引：3
|
作者：
Grant, AS [1 ]
Chaudhary, K
Stewart, L
Peters, A
Delisle, S
Decken, A
机构：
[1] Mt Allison Univ, Dept Chem, Sackville, NB E4L 1G8, Canada
[2] Univ Winnipeg, Dept Chem, Winnipeg, MB R3B 2E9, Canada
[3] Univ New Brunswick, Dept Chem, Fredericton, NB E3B 6E2, Canada
来源：
TETRAHEDRON LETTERS | 2004年 / 45卷 / 08期
基金：
加拿大自然科学与工程研究理事会;
关键词：
organic synthesis; bioorganic;
D O I：
10.1016/j.tetlet.2003.12.087
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A facile, racemic synthesis of a 'twisted' transition-state analogue of biotin is described. A key reaction is the electronically assisted ring-closure of the sulfur containing ring by displacement of an in situ generated mesylate by a suitably positioned 4-methoxybenzyl sulfide. The crystal structure of tricyclic compound 6 shows the AB ring system to indeed be twisted. The 'twist' was introduced to examine the possible involvement of sulfur participation in biotin biochemistry. (C) 2003 Elsevier Ltd. All rights reserved.
引用
收藏
页码：1777 / 1780
页数：4
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