Enantioselective synthesis of the bicyclo[4.3.0]nonane ring system of the pinguisane-type sesquiterpenoids via a Bronsted acid promoted transannular enol alkylation

被引:12
作者
Clarke, PA [1 ]
Black, RJG [1 ]
Blake, AJ [1 ]
机构
[1] Univ Nottingham, Sch Chem, Nottingham NG7 2RD, England
基金
英国工程与自然科学研究理事会;
关键词
pinguisane sesquiterpenoids; transannular cyclisations; enol alkylation; Bronsted acid; vicinal quaternary centres;
D O I
10.1016/j.tetlet.2005.12.084
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The bicyclo[4.3.0]nonane ring system of the pinguisane-type sesquiterpenoid natural products, including the vicinal quaternary stereocentres, has been synthesised as a single enantiomer via a novel Bronsted acid promoted transannular alkylation of an enol with an unactivated alkene. (c) 2006 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1453 / 1455
页数:3
相关论文
共 22 条
[1]  
ASAKAWA Y, 1976, Tetrahedron Letters, V40, P3619
[2]  
Asakawa Y., 1995, Progress in the Chemistry of Organic Natural Products, V65, P1
[3]  
BELKIN M, 1952, J NATL CANCER I, V13, P741
[4]   Synthetic studies on the DEF-rings of FR182877 and hexacyclinic acid [J].
Clarke, PA ;
Grist, M ;
Ebden, M ;
Wilson, C ;
Blake, AJ .
TETRAHEDRON, 2005, 61 (02) :353-363
[5]   An iodocyclisation/elimination approach to a DEF-ring core of FR182877 [J].
Clarke, PA ;
Grist, M ;
Ebden, M .
TETRAHEDRON LETTERS, 2004, 45 (05) :927-929
[6]   Synthesis of a model DEF-ring core of hexacyclinic acid [J].
Clarke, PA ;
Grist, M ;
Ebden, M ;
Wilson, C .
CHEMICAL COMMUNICATIONS, 2003, (13) :1560-1561
[7]   Asymmetric aldol additions:: Use of titanium tetrachloride and (-)-sparteine for the soft enolization of N-acyl oxazolidinones, oxazolidinethiones, and thiazolidinethiones [J].
Crimmins, MT ;
King, BW ;
Tabet, EA ;
Chaudhary, K .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (03) :894-902
[8]   SYNTHESIS OF SESQUITERPENE (+/-)-CHILOSCYPHONE [J].
GERLING, KG ;
WOLF, H .
TETRAHEDRON LETTERS, 1985, 26 (10) :1293-1294
[9]   Total synthesis of 7-O-methyldehydropinguisenol by palladium-catalyzed 1,7-enyne cycloisomerization [J].
Harada, K ;
Tonoi, Y ;
Kato, H ;
Fukuyama, Y .
TETRAHEDRON LETTERS, 2002, 43 (21) :3829-3832
[10]   Two novel Diels-Alder reaction-type dimeric pinguisane sesquiterpenoids and related compounds from the liverwort Porella acutifolia subsp. tosana [J].
Hashimoto, T ;
Irita, H ;
Tanaka, M ;
Takaoka, S ;
Asakawa, Y .
TETRAHEDRON LETTERS, 1998, 39 (19) :2977-2980