THE [2,3]-WITTIG REARRANGEMENT ROUTE TOWARD ANNONACEOUS ACETOGENINS FROM FURANOID GLYCALS - A PRELIMINARY-STUDY

被引:11
作者
BERTRAND, P [1 ]
GESSON, JP [1 ]
RENOUX, B [1 ]
TRANOY, I [1 ]
机构
[1] UNIV POITIERS, CNRS, CHIM LAB 12, F-86022 POITIERS, FRANCE
关键词
D O I
10.1016/0040-4039(95)00684-5
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The [2,3]-Wittig rearrangement of trimethylsilylpropargyl ethers of furanoid glycals derived from D-mannose and L-gulonic gamma-lactone affords cis 2,5-disubstituted dihydrofurans with predominant erythro selectivity. Under the same conditions, [1,2]-Wittig rearrangement is observed with a glycal derived from D-ribonic gamma-lactone.
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收藏
页码:4073 / 4076
页数:4
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共 26 条
[1]  
Rupprecht, Hui, McLaughlin, J. Nat. Prod., 53, pp. 237-278, (1990)
[2]  
Cave, Cortes, Figadere, Hocquemiller, Laprevote, Laurens, Leboeuf, Recent Advances in the Acetogenins of Annonaceae, Phytochemical Potential of Tropical Plants, pp. 167-202, (1993)
[3]  
Fang, Rieser, Gu, Zhao, McLaughlin, Phytochem. Anal., 4, pp. 27-67, (1993)
[4]  
McCloud, Smith, Chang, Cassady, Experientia, 43, pp. 947-949, (1987)
[5]  
Rieser, Hui, Rupprecht, Kozlowski, Wood, McLaughlin, Hanson, Zhuang, Hoye, J. Am. Chem. Soc., 114, pp. 10203-10213, (1992)
[6]  
Gu, Zeng, Fang, Colman-Saizarbitoria, Huo, McLaughlin, J. Org. Chem., 59, pp. 5162-5172, (1994)
[7]  
Pettit, Cragg, Polonsky, Herald, Goswami, Smith, Moretti, Schmidt, Weisleder, Can. J. Chem., 65, (1987)
[8]  
Alkofahi, Rupprecht, Liu, Chang, Smith, McLaughlin, Experientia, 46, pp. 539-541, (1990)
[9]  
Yu, Hu, Ho, Bezan, Stephens, Cassady, Brinen, Clardy, J. Org. Chem., 59, pp. 1598-1599, (1994)
[10]  
Figadere, Cave, Total Stereoselective Synthesis of Acetogenins of Annonaceae: a New Class of Bioactive Polyketides, Studies in Natural Products: Stereoselective Synthesis, (1995)