Formation of orthoesters in the sharpless asymmetric epoxidation : hemisynthesis of labdanes
作者： J.G. Urones , I.S. Marcos , P. Basabe , Mª J. Sexmero , D. Diez
DOI: 10.1016/S0040-4020(01)82030-5
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摘要: Abstract The orthoesters, 4a and 4b were obtained from treatment of methyl-7,13E-labdadien-17-oate, 3, under Sharpless asymmetric epoxidation conditions . hydrolysis followed by dehydration the orthoesters led to synthesis two new diterpenic acids isolated Halimium viscosum : 14R,15-dihydroxy-7,13(16)-labdadien-17-oic 14S,15.dihydroxy-7, 13(16)-labdadien-17-oic.
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sci-hub.se 参考文章(14)
J. K. Crandall, Luan-Ho Chang Lin, Base-promoted reactions of epoxides. V. 1-Alkylcycloalkene oxides Journal of Organic Chemistry. ,vol. 33, pp. 2375- 2378 ,(1968) , 10.1021/JO01270A043
Julio G Urones, Isidro Sánchez Marcos, David Diez Martin, FMS Brito Palma, Jesús M Rodilla, None, Labdane diterpenoids from Halimium viscosum and H. verticilatum Phytochemistry. ,vol. 26, pp. 3037- 3040 ,(1987) , 10.1016/S0031-9422(00)84588-4
Jack E. Baldwin, Richard C. Thomas, Lawrence I. Kruse, Lee Silberman, Rules for ring closure: ring formation by conjugate addition of oxygen nucleophiles Journal of Organic Chemistry. ,vol. 42, pp. 3846- 3852 ,(1977) , 10.1021/JO00444A011
J.G. Urones, I.S. Marcos, D. Díez Martín, Transformatiom of labdanes into drimanes:obtention of 11-12-diacetoxy-7-drimene, precursor of biologically active drimanes Tetrahedron. ,vol. 44, pp. 4547- 4554 ,(1988) , 10.1016/S0040-4020(01)86157-3
Robert M. Hanson, Absolute stereochemistry of the triol moiety of gymnoprenols: a reinvestigation Tetrahedron Letters. ,vol. 25, pp. 3783- 3786 ,(1984) , 10.1016/S0040-4039(01)91166-9
Pierre Deslongchamps, Daniel Guay, Robert Chènevert, The hydrolysis of cis and trans methoxy bicyclic and tricyclic orthoesters. Evidence for a chair–boat inversion prior to breakdown in some hemiorthoester tetrahedral intermediates Canadian Journal of Chemistry. ,vol. 63, pp. 2493- 2500 ,(1985) , 10.1139/V85-413
Pierre Deslongchamps, Jean Lessard, Yves Nadeau, The products of hydrolysis of cyclic orthoesters as a function of pH and the theory of stereoelectronic control Canadian Journal of Chemistry. ,vol. 63, pp. 2485- 2492 ,(1985) , 10.1139/V85-412
James Dillon, Koji Nakanishi, Absolute configurational studies of vicinal glycols and amino alcohols. II. With tris(dipivalomethanato)praseodymium Journal of the American Chemical Society. ,vol. 97, pp. 5417- 5422 ,(1975) , 10.1021/JA00852A016
E. J. Corey, Shunichi Hashimoto, Alan E. Barton, Chirally directed synthesis of (-)-methyl 5(S), 6(S)-oxido-7-hydroxyheptanoate, a key intermediate for the total synthesis of leukotrienes A, C, D and E Journal of the American Chemical Society. ,vol. 103, pp. 721- 722 ,(1981) , 10.1021/JA00393A063
K. B. Sharpless, M. Caron, Ti(O-i-Pr)4-mediated nucleophilic openings of 2,3-epoxy alcohols. A mild procedure for regioselective ring-opening Journal of Organic Chemistry. ,vol. 50, pp. 1557- 1560 ,(1985)