Asymmetric synthesis of all the stereoisomers of tarchonanthuslactone

被引:26
作者
Baktharaman, S [1 ]
Selvakumar, S [1 ]
Singh, VK [1 ]
机构
[1] Indian Inst Technol, Dept Chem, Kanpur 208016, Uttar Pradesh, India
关键词
tarchonanthuslactone; asymmetric synthesis; Kulinkovich reaction; RCM;
D O I
10.1016/j.tetlet.2005.08.164
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
We describe herein an efficient synthesis of all the four stereoisomers of tarchonanthuslactone from (R)-3-hydroxy butanoate, easily prepared from L-threonine. The approach involves the use of a beta,gamma-unsaturated delta-lactone as an intermediate, obtained via a Kulinkovich reaction followed by a ring-closing metathesis strategy. (c) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码:7527 / 7529
页数:3
相关论文
共 31 条
[1]  
ADITYACHAUDHURY N, 1979, J SCI IND RES INDIA, V38, P265
[2]   NATURALLY OCCURRING TERPENE DERIVATIVES .189. NEW BISABOLENE DERIVATIVE AND NEW DIHYDROCAFFEIC ACID-DERIVATIVE FROM TARCHONANTHUSTRILOBUS [J].
BOHLMANN, F ;
SUWITA, A .
PHYTOCHEMISTRY, 1979, 18 (04) :677-678
[3]   Total synthesis of (+)-boronolide, (+)-deacetylboronolide, and (+)-dideacetylboronolide [J].
Chandrasekhar, M ;
Chandra, KL ;
Singh, VK .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (10) :4039-4045
[4]   Formal total synthesis of (+)-boronolide [J].
Chandrasekhar, M ;
Raina, S ;
Singh, VK .
TETRAHEDRON LETTERS, 2000, 41 (25) :4969-4971
[5]  
Davies-Coleman M T, 1989, Fortschr Chem Org Naturst, V55, P1
[6]   Synthesis of oxygen- and nitrogen-containing heterocycles by ring-closing metathesis [J].
Deiters, A ;
Martin, SF .
CHEMICAL REVIEWS, 2004, 104 (05) :2199-2238
[7]   REACTIONS OF CYCLOPROPANOLS WITH HALOGENATING AGENTS AND OTHER ELECTROPHILES [J].
DEPUY, CH ;
VANLANEN, RJ .
JOURNAL OF ORGANIC CHEMISTRY, 1974, 39 (23) :3360-3365
[8]   An efficient asymmetric synthesis of tarchonanthuslactone [J].
Enders, D ;
Steinbusch, D .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2003, 2003 (22) :4450-4454
[9]   An enantioselective synthesis of tarchonanthuslactone [J].
Garaas, SD ;
Hunter, TJ ;
O'Doherty, GA .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (08) :2682-2685
[10]  
GRUBBS RH, 2003, HDB METATHESIS, V1, pCH10