Enantiospecific syntheses of (3S,4R)- and (3S,4R,7S)-diastereoisomers of goniofufurone

作者: Tony K.M. Shing , Hon-Chung Tsui

DOI: 10.1016/0957-4166(94)80168-1

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摘要: Abstract D -Mannose has been converted by six sequential reactions (acetonation, Wittig-intramolecular Michael reaction, selective deacetonation, glycol cleavage oxidation and Grignard reaction) into the methyl esters 9 10 which underwent a de-isopropylidenation reaction with concommitant lactonisation to give (3 S ,4 R )- ,7 )-diastereoisomers of goniofufurone 1 2 .

参考文章(13)
Xin-Ping Fang, Jon E. Anderson, Ching-Jer Chang, Jerry L. McLaughlin, Phillip E. Fanwick, Two new styryl lactones, 9-deoxygoniopypyrone and 7-epi-goniofufurone, from Goniothalamus giganteus. Journal of Natural Products. ,vol. 54, pp. 1034- 1043 ,(1991) , 10.1021/NP50076A017
Zhou Wei-Shan, Yang Zhi-Cai, Asymmetric total synthesis of (+)-goniopypyrone Tetrahedron Letters. ,vol. 34, pp. 7075- 7076 ,(1993) , 10.1016/S0040-4039(00)61602-7
Hiroshi Ohrui, Gordon H. Jones, John G. Moffatt, Michael L. Maddox, Arild T. Christensen, Susan K. Byram, C-glycosyl nucleosides. V. Some unexpected observations on the relative stabilities of compounds containing fused five-membered rings with epimerizable substituents. Journal of the American Chemical Society. ,vol. 97, pp. 4602- 4613 ,(1975) , 10.1021/JA00849A023
Tony K.M. Shing, Zhao-hui Zhou, Goniotriol and 8-acetylgoniotriol: syntheses and absolute configurations Tetrahedron Letters. ,vol. 33, pp. 3333- 3334 ,(1992) , 10.1016/S0040-4039(00)92081-1
Tony K.M. Shing, Tsui Hon-Chung, Zhou Zhao-Hui, First total synthesis of potent antitumour agent (+)-goniopypyrone Tetrahedron Letters. ,vol. 34, pp. 691- 692 ,(1993) , 10.1016/S0040-4039(00)61654-4
A. Alkofahi, W.-W. Ma, A. T. McKenzie, S. R. Byrn, J. L. McLaughlin, Goniotriol from Goniothalamus giganteus. Journal of Natural Products. ,vol. 52, pp. 1371- 1373 ,(1989) , 10.1021/NP50066A037
Tony K.M. Shing, Hon-Chung Tsui, Zhao-Hui Zhou, Stereocontrolled syntheses of (-)-goniofufurone and (-)-8-epi-goniofufurone Tetrahedron. ,vol. 48, pp. 8659- 8666 ,(1992) , 10.1016/S0040-4020(01)89441-2
Jianhua Ye, Rama K. Bhatt, J.R. Falck, Stereospecific α-alkoxystannane couplings with acyl chlorides: Total synthesis of (+)-goniofufurone Tetrahedron Letters. ,vol. 34, pp. 8007- 8010 ,(1993) , 10.1016/S0040-4039(00)61436-3