The first construction of the B,C,D-ring fragment of pinnatoxins via highly stereocontrolled acetallization

被引:38
作者
Sugimoto, T [1 ]
Ishihara, J [1 ]
Murai, A [1 ]
机构
[1] HOKKAIDO UNIV,GRAD SCH SCI,DIV CHEM,SAPPORO,HOKKAIDO 060,JAPAN
关键词
D O I
10.1016/S0040-4039(97)01725-5
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The synthesis of the B,C,D-ring fragment of pinnatoxins is described. The highly stereocontrolled construction of the 6,5,6-tris-spiroacetal core was achieved on treatment of compound 3 with aqueous HF in CH3CN. The anomeric effect at C-16 enhanced by neighboring carbonyl group led to form the tris-spiroacetal having the natural configuration. (C) 1997 Elsevier Science Ltd.
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页码:7379 / 7382
页数:4
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