Tandem addition-cyclization mediated by sulfanyl radicals:: a versatile strategy for iridoids synthesis

被引：12
|
作者：
Sanchez, Elena M. [1 ]
Arteaga, Jesus F. [1 ]
Domingo, Victor [1 ]
del Moral, Jose F. Quilez [1 ]
Herrador, M. Mar [1 ]
Barrero, Alejandro F. [1 ]
机构：
[1] Univ Granada, Inst Biotechnol, Dept Organ Chem, E-18071 Granada, Spain
来源：
TETRAHEDRON | 2008年 / 64卷 / 22期
关键词：
sulfanyl radical; radical cyclizations; iridanes; enantioselective synthesis;
D O I：
10.1016/j.tet.2008.03.058
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Sulfanyl radicals trigger a tandem addition-cyclization protocol in linalool or Citronelene derivatives for the efficient construction of the iridane monoterpene skeleton. Best results in yields and diastereoselectivity were obtained when phenylethylsulfanyl was used as radical initiator. We have proved the utility of this protocol with the enantiospecific synthesis of natural iridane dehydroiridomyrmecin starting from a (-)-linalyl acetate ester derivative in five steps with a 28% overall yield. (c) 2008 Elsevier Ltd. All rights reserved.
引用
收藏
页码：5111 / 5118
页数：8
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