Stereoselective synthesis of the C1-C13 fragment of (+)-discodermolide using asymmetric allyltitanations

被引:33
作者
BouzBouz, S [1 ]
Cossy, J [1 ]
机构
[1] Ecole Super Phys & Chim Ind Ville Paris, CNRS, Chim Organ Lab, F-75231 Paris 05, France
关键词
D O I
10.1021/ol034958l
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
graphic The synthesis of the C1-C13 fragment of (+)-discodermolide has been achieved. The configurations of the stereogenic centers have been controlled by enantioselective allyl- and crotyltitanations of aldehydes, and the Z configuration of the olefin at C8-C9 was controlled by a ring-closing metathesis.
引用
收藏
页码:3029 / 3031
页数:3
相关论文
共 26 条
[1]   Selective dihydroxylation of non-conjugated dienes in favor of the terminal olefin [J].
Andrus, MB ;
Lepore, SD ;
Sclafani, JA .
TETRAHEDRON LETTERS, 1997, 38 (23) :4043-4046
[2]  
[Anonymous], [No title captured], Patent No. 5840750
[3]   Studies directed toward the total synthesis of discodermolide: Asymmetric synthesis of the C1-C14 fragment [J].
Arefolov, A ;
Panek, JS .
ORGANIC LETTERS, 2002, 4 (14) :2397-2400
[4]   SYNTHESIS OF THE LOWER SUBUNIT OF RHIZOXIN [J].
BOGER, DL ;
CURRAN, TT .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (08) :2235-2244
[5]   Efficient strategy for the synthesis of stereopentad subunits of scytophycin, rifamycin S, and discodermolide [J].
BouzBouz, S ;
Cossy, J .
ORGANIC LETTERS, 2001, 3 (25) :3995-3998
[6]   Formal synthesis of (+)-discodermolide [J].
Francavilla, C ;
Chen, WC ;
Kinder, FR .
ORGANIC LETTERS, 2003, 5 (08) :1233-1236
[7]   IMMUNOSUPPRESSIVE COMPOUNDS FROM A DEEP-WATER MARINE SPONGE, AGELAS-FLABELLIFORMIS [J].
GUNASEKERA, SP ;
CRANICK, S ;
LONGLEY, RE .
JOURNAL OF NATURAL PRODUCTS, 1989, 52 (04) :757-761
[8]   CORRECTION [J].
GUNASEKERA, SP .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (03) :1346-1346
[9]   ENANTIOSELECTIVE ALLYLTITANATION OF ALDEHYDES WITH CYCLOPENTADIENYLDIALKOXYALLYLTITANIUM COMPLEXES [J].
HAFNER, A ;
DUTHALER, RO ;
MARTI, R ;
RIHS, G ;
ROTHESTREIT, P ;
SCHWARZENBACH, F .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (07) :2321-2336
[10]  
HALSTEAD DP, 1998, THESIS HARVARD U CAM