Development of an access route to the C31-C52 central core of amphidinol 3

被引:30
作者
Bedore, Matthew W. [1 ]
Chang, Shuh-Kuen [1 ]
Paquette, Leo A. [1 ]
机构
[1] Ohio State Univ, Evans Chem Labs, Columbus, OH 43210 USA
关键词
D O I
10.1021/ol062875+
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An asymmetric synthesis of the heavily oxygenated inner sector of amphidinol 3 constituted of C31-C52 is described. The successful pathway highlights construction of the pair of identical tetrahydropyran subunits from a common intermediate.
引用
收藏
页码:513 / 516
页数:4
相关论文
共 40 条
[1]   NOVEL CONVERSION OF EPOXIDES TO ONE-CARBON HOMOLOGATED ALLYLIC ALCOHOLS BY DIMETHYLSULFONIUM METHYLIDE [J].
ALCARAZ, L ;
HARNETT, JJ ;
MIOSKOWSKI, C ;
MARTEL, JP ;
LEGALL, T ;
SHIN, DS ;
FALCK, JR .
TETRAHEDRON LETTERS, 1994, 35 (30) :5449-5452
[2]  
BLUNDELL P, 1994, SYNLETT, P263
[3]   Chemoselective cross-metathesis reaction. Application to the synthesis of the C1-C14 fragment of amphidinol 3 [J].
BouzBouz, S ;
Cossy, J .
ORGANIC LETTERS, 2001, 3 (10) :1451-1454
[4]  
BRANDSMA L, 1987, PREPARATIVE POLAR OR, V1, P63
[5]   ENANTIOSELECTIVE TOTAL SYNTHESIS OF 9S-DIHYDROERYTHRONOLIDE-A SECO ACID [J].
CHAMBERLIN, AR ;
DEZUBE, M ;
REICH, SH ;
SALL, DJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (16) :6247-6256
[6]  
CHANG SK, 2006, THESIS OHIO STATE U
[7]   SILYLSTANNANES IN ORGANIC-SYNTHESIS - SCOPE AND LIMITATION OF PALLADIUM-CATALYZED REACTION WITH ACETYLENES [J].
CHENARD, BL ;
VANZYL, CM .
JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (19) :3561-3566
[8]   SILYLSTANNANES - USEFUL REAGENTS FOR BIS FUNCTIONALIZATION OF ALPHA-UNSATURATED, BETA-UNSATURATED KETONES AND ACETYLENES [J].
CHENARD, BL ;
LAGANIS, ED ;
DAVIDSON, F ;
RAJANBABU, TV .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (19) :3666-3667
[9]   Recent advances in the synthetic applications of the oxazaborolidine-mediated asymmetric reduction [J].
Cho, Byung Tae .
TETRAHEDRON, 2006, 62 (33) :7621-7643
[10]  
Corey EJ, 1998, ANGEW CHEM INT EDIT, V37, P1987, DOI 10.1002/(SICI)1521-3773(19980817)37:15<1986::AID-ANIE1986>3.0.CO