Claisen orthoester rearrangement in the direct preparation of Z-isositsirikine and Z-geissoschizine derivatives possessing the right oxidation state at C-17
M Lounasmaa, P Hanhinen, R Jokela
Index: Lounasmaa, Mauri; Hanhinen, Pirjo; Jokela, Reija Tetrahedron, 1995 , vol. 51, # 31 p. 8623 - 8648
Full Text: HTML
Citation Number: 11
Abstract
The Claisen orthoester rearrangement utilizing allylic alcohol 1 (or 2) and trimethyl 3- methoxyortbopropionate 13a leads to Z-isositsirikine derivatives 21a–22a (or 23a–24a) possessing one RO-function at C-17. In the cases of trialkyl 3, 3-dialkoxyorthopropionates [triethyl 3, 3-diethoxyorthopropionate 14b (or 3, 3-diethoxymethylketene diethylacetal 20b) and trimethyl 3, 3-dimethoxyorthopropionate 14 a (or 3, 3-dimethoxymethylketene ...
Related Articles:
[Heasley, Victor L.; Wade, Kimberley E.; Aucoin, Thomas G.; Gipe, Daphne E.; Shellhamer Dale F.; Heasley, Gene E. Journal of Organic Chemistry, 1983 , vol. 48, # 8 p. 1377 - 1379]
Communications-Halogenation of Unsaturated Aldehydes with Cupric Halides
[Castro,C.E. Journal of Organic Chemistry, 1961 , vol. 26, p. 4183 - 4184]