Stereoselective syntheses of the C′D′E′F′-ring system of maitotoxin and the FG-ring system of gambierol

被引:56
作者
Sakamoto, Y [1 ]
Matsuo, G [1 ]
Matsukura, H [1 ]
Nakata, T [1 ]
机构
[1] RIKEN, Inst Phys & Chem Res, Wako, Saitama 3510198, Japan
关键词
D O I
10.1021/ol016355k
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] The stereoselective syntheses of the C 'D 'E 'F ' -ring system of maitotoxin and the FG-ring system of gambierol were accomplished. The key steps involve 6-endo-cyclization of methylepoxide, Sml(2)-induced reductive cyclization, 6-endo-cyclization of vinylepoxide, and formation of the lactone ring.
引用
收藏
页码:2749 / 2752
页数:4
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共 50 条
[1]   The stereochemical assignment and conformational analysis of the V/W-ring juncture of maitotoxin [J].
Cook, LR ;
Oinuma, H ;
Semones, MA ;
Kishi, Y .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (34) :7928-7937
[2]   TOTAL SYNTHESIS OF VENUSTATRIOL [J].
COREY, EJ ;
HA, DC .
TETRAHEDRON LETTERS, 1988, 29 (26) :3171-3174
[3]   Synthetic studies on a marine polyether toxin, gambierol:: stereoselective synthesis of the FGH ring system via B-alkyl Suzuki coupling [J].
Fuwa, H ;
Sasaki, M ;
Tachibana, K .
TETRAHEDRON LETTERS, 2000, 41 (43) :8371-8375
[4]   Synthetic studies on a marine polyether toxin, gambierol:: stereoselective synthesis of the EFGH ring system via B-alkyl Suzuki coupling [J].
Fuwa, H ;
Sasaki, M ;
Tachibana, K .
TETRAHEDRON, 2001, 57 (15) :3019-3033
[5]   MAITOTOXIN - A UNIQUE PHARMACOLOGICAL TOOL FOR RESEARCH ON CALCIUM-DEPENDENT MECHANISMS [J].
GUSOVSKY, F ;
DALY, JW .
BIOCHEMICAL PHARMACOLOGY, 1990, 39 (11) :1633-1639
[6]   Efficient synthesis of 2,3-trans-tetrahydropyrans and oxepanes:: Rearrangement-ring expansion of cyclic ethers having a chloromethanesulfonate [J].
Hori, N ;
Nagasawa, K ;
Shimizu, T ;
Nakata, T .
TETRAHEDRON LETTERS, 1999, 40 (11) :2145-2148
[7]   An efficient strategy for the iterative synthesis of a trans-fused polytetrahydropyran ring system via SmI2-induced reductive intramolecular cyclization [J].
Hori, N ;
Matsukura, H ;
Matsuo, G ;
Nakata, T .
TETRAHEDRON LETTERS, 1999, 40 (14) :2811-2814
[8]   Efficient synthesis of trans-fused polycyclic ethers including tetrahydropyrans and oxepanes based on SmI2-induced reductive cyclization [J].
Hori, N ;
Matsukura, H ;
Nakata, T .
ORGANIC LETTERS, 1999, 1 (07) :1099-1101
[9]   A novel convergent approach to trans-fused polyether frameworks based on the reaction of vinylstannanes and triflates and its application to a synthetic study of the EFGH ring system of gambierol [J].
Kadowaki, C ;
Chan, PWH ;
Kadota, I ;
Yamamoto, Y .
TETRAHEDRON LETTERS, 2000, 41 (30) :5769-5772
[10]  
KAGAN HB, 1990, NEW J CHEM, V14, P453