TOTAL SYNTHESIS OF HALICHONDRINS - ENANTIOSELECTIVE CONSTRUCTION OF A HOMOCHIRAL TETRACYCLIC KLMN-RING INTERMEDIATE FROM D-MANNITOL

被引:25
作者
DIFRANCO, E [1 ]
RAVIKUMAR, VT [1 ]
SALOMON, RG [1 ]
机构
[1] CASE WESTERN RESERVE UNIV,DEPT CHEM,CLEVELAND,OH 44106
关键词
D O I
10.1016/S0040-4039(00)73673-2
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient strategy exploiting C2 symmetry and featuring diastereoselective conjugate addition of Li2Me2CuCN to a gamma-alkoxy-alpha,beta-unsaturated acylsilane and diastereoselective spiroketalization provides a key tetracyclic KLMN-ring intermediate for halichondrin B from D-mannitol.
引用
收藏
页码:3247 / 3250
页数:4
相关论文
共 20 条
[1]   TOTAL SYNTHESIS OF HALICHONDRIN-B AND NORHALICHONDRIN-B [J].
AICHER, TD ;
BUSZEK, KR ;
FANG, FG ;
FORSYTH, CJ ;
JUNG, SH ;
KISHI, Y ;
MATELICH, MC ;
SCOLA, PM ;
SPERO, DM ;
YOON, SK .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (08) :3162-3164
[2]   NAZAROV CYCLIZATION OF DIENONE-ESTERS AND TETRAHYDROPYRONES USING TRIMETHYLSILYLTRIFLATE [J].
ANDREWS, JFP ;
REGAN, AC .
TETRAHEDRON LETTERS, 1991, 32 (52) :7731-7734
[3]   NEW METHOD FOR DEOXYGENATION OF SECONDARY ALCOHOLS [J].
BARTON, DHR ;
MCCOMBIE, SW .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1975, (16) :1574-1585
[4]  
BESTMANN HJ, 1979, SYNTHESIS-STUTTGART, P201
[5]  
COOPER AJ, 1990, TETRAHEDRON LETT, V30, P3813
[6]  
HIRANO S, 1974, TETRAHEDRON LETT, P1429
[7]   HALICHONDRINS - ANTITUMOR POLYETHER MACROLIDES FROM A MARINE SPONGE [J].
HIRATA, Y ;
UEMURA, D .
PURE AND APPLIED CHEMISTRY, 1986, 58 (05) :701-710
[8]   TOTAL SYNTHESIS OF HALICHONDRINS - HIGHLY STEREOSELECTIVE CONSTRUCTION OF A HOMOCHIRAL PENTASUBSTITUTED H-RING PYRAN INTERMEDIATE FROM ALPHA-D-GLUCOSE [J].
KIM, S ;
SALOMON, RG .
TETRAHEDRON LETTERS, 1989, 30 (46) :6279-6282
[9]   SYNTHESIS OF 1,4-DIEN-3-ONES AND 2-CYCLOPENTENONES [J].
KJELDSEN, G ;
KNUDSEN, JS ;
RAVNPETERSEN, LS ;
TORSSELL, KBG .
TETRAHEDRON, 1983, 39 (13) :2237-2239
[10]   NEW DERIVATIVES OF 2,5-ANHYDRO-D-HEXITOLS .1. ISOLATION OF 2,5-ANHYDRO-1,3-O-ISOPROPYLIDENE-6-O-TRITYL-D-GLUCITOL AND CONFORMATIONS OF ITS 4-O-SUBSTITUTED AND DEPROTECTED, ACYLATED DERIVATIVES [J].
KOERNER, TAW ;
VOLL, RJ ;
YOUNATHAN, ES .
CARBOHYDRATE RESEARCH, 1977, 59 (02) :403-416