Asymmetric synthesis of (-)-dihydroxanthatin by the stereloselective Oshima-Utimoto reaction

被引:59
作者
Evans, MA [1 ]
Morken, JP [1 ]
机构
[1] Univ N Carolina, Dept Chem, Chapel Hill, NC 27599 USA
关键词
D O I
10.1021/ol051276k
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The catalytic stereoselective Oshima-Utimoto reaction is useful for the construction of five-membered oxacycles from simple starting materials and was employed for the preparation of the lactone group in the asymmetric synthesis of (-)-11 alpha,13-dihydroxanthatin. Completion of the synthesis is facilitated by ring-closing enyne metathesis and alkene cross metathesis reactions.
引用
收藏
页码:3371 / 3373
页数:3
相关论文
共 32 条
[1]  
[Anonymous], 1984, ASYMMETRIC SYNTHESIS
[2]   HORNER-WADSWORTH-EMMONS REACTION - USE OF LITHIUM-CHLORIDE AND AN AMINE FOR BASE SENSITIVE COMPOUNDS [J].
BLANCHETTE, MA ;
CHOY, W ;
DAVIS, JT ;
ESSENFELD, AP ;
MASAMUNE, S ;
ROUSH, WR ;
SAKAI, T .
TETRAHEDRON LETTERS, 1984, 25 (21) :2183-2186
[3]   POTENTIAL ANTI-TUMOR AGENTS - SYNTHESIS, REACTIVITY, AND CYTOTOXICITY OF ALPHA-METHYLENE CARBONYL-COMPOUNDS [J].
CASSADY, JM ;
BYRN, SR ;
STAMOS, IK ;
EVANS, SM ;
MCKENZIE, A .
JOURNAL OF MEDICINAL CHEMISTRY, 1978, 21 (08) :815-819
[4]   HIGHLY ENANTIOSELECTIVE BORANE REDUCTION OF KETONES CATALYZED BY CHIRAL OXAZABOROLIDINES - MECHANISM AND SYNTHETIC IMPLICATIONS [J].
COREY, EJ ;
BAKSHI, RK ;
SHIBATA, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (18) :5551-5553
[5]  
DESS DB, 1983, J ORG CHEM, V48, P4156
[6]   XANTHININ .2. THE STRUCTURES OF XANTHININ AND XANTHATIN [J].
DEUEL, PG ;
GEISSMAN, TA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1957, 79 (14) :3778-3783
[7]   A GENERAL ENTRY TO GUAIANOLIDES - AN ILLUSTRATIVE SYNTHESIS OF (+/-)-COMPRESSANOLIDE [J].
DEVREESE, AA ;
DECLERCQ, PJ ;
VANDEWALLE, M .
TETRAHEDRON LETTERS, 1980, 21 (49) :4767-4770
[8]   Enyne metathesis (enyne bond reorganization) [J].
Diver, ST ;
Giessert, AJ .
CHEMICAL REVIEWS, 2004, 104 (03) :1317-1382
[9]   Stereoselective synthesis of furans by the Pd-catalyzed Oshima-Utimoto reaction [J].
Evans, MA ;
Morken, JP .
ORGANIC LETTERS, 2005, 7 (15) :3367-3370
[10]   ONE-POT SYNTHESIS OF TETRAHYDROFURAN DERIVATIVES FROM ALLYLIC ALCOHOLS AND VINYL ETHERS BY MEANS OF PALLADIUM(II) ACETATE [J].
FUGAMI, K ;
OSHIMA, K ;
UTIMOTO, K .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1989, 62 (06) :2050-2054