Enantioselective total synthesis of (-)-xialenon A

被引:10
作者
Hodgson, DM [1 ]
Galano, JM [1 ]
Christlieb, M [1 ]
机构
[1] Univ Oxford, Dyson Perrins Lab, Dept Chem, Oxford OX1 3QY, England
关键词
D O I
10.1039/b208485f
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The first total synthesis of (-)-xialenon A (1) via conjugate allylation of a 1,5-cyclooctadiene-derived bicyclo[3.3.0]octenone 3 and an alpha'-hydroxylation on the more hinderd face of enone 9 using hypervalent iodine chemistry, is described.
引用
收藏
页码:2436 / 2437
页数:2
相关论文
共 18 条
[1]  
DEMIR AS, 1992, SYNTHESIS-STUTTGART, P235
[2]  
HELMCHEN G, 1974, TETRAHEDRON LETT, P1527
[3]   Functionalised bicyclic alcohols by enantioselective α-deprotonation-rearrangement of meso-epoxides [J].
Hodgson, DM ;
Cameron, ID ;
Christlieb, M ;
Green, R ;
Lee, GP ;
Robinson, LA .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2001, (18) :2161-2174
[4]  
Hodgson DM, 2002, SYNTHESIS-STUTTGART, P1625
[5]   Functionalized bicyclo[3.3.0]octanes by enantioselective transannular desymmetrization [J].
Hodgson, DM ;
Cameron, ID .
ORGANIC LETTERS, 2001, 3 (03) :441-444
[6]   SYNTHESIS OF ALPHA,BETA-UNSATURATED CARBONYL-COMPOUNDS BY PALLADIUM(II)-CATALYZED DEHYDROSILYLATION OF SILYL ENOL ETHERS [J].
ITO, Y ;
HIRAO, T ;
SAEGUSA, T .
JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (05) :1011-1013
[7]  
LEY SV, 1994, SYNTHESIS-STUTTGART, P639
[8]   NEW METHODOLOGY FOR CONJUGATE ADDITIONS OF ALLYLIC LIGANDS TO ALPHA,BETA-UNSATURATED KETONES - SYNTHETIC AND SPECTROSCOPIC STUDIES [J].
LIPSHUTZ, BH ;
ELLSWORTH, EL ;
DIMOCK, SH ;
SMITH, RAJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (11) :4404-4410
[9]  
Moriarty RM, 1999, ORG REACTIONS, V54, P273, DOI DOI 10.1002/0471264180.0R054.02
[10]  
Nicolaou KC, 2002, ANGEW CHEM INT EDIT, V41, P996, DOI 10.1002/1521-3773(20020315)41:6<996::AID-ANIE996>3.0.CO