Abstract:
The Wittig reaction of {(1S,4R,5R)-5-[(tert-butyldimethylsilyloxy) methyl]-4-hydroxycyclopent-2-en-1-yl}acetaldehyde is accompanied by the migration of silyl protective group from the primary hydroxy group to the secondary one, which enables further synthesis of J-type prostaglandins. Study of this phenomemon on model relative ester comprising base variation revealed formation of unusual functionalized bicyclo[3.1.0]hex-2-ene-6-carboxylate derivative.
Citation:
A. M. Gimazetdinov, A. Z. Al'mukhametov, V. V. Zagitov, M. S. Miftakhov, “Formal synthesis of J-type prostaglandins based on enantiopure polyfunctional cyclopentenol derivative”, Mendeleev Commun., 31:2 (2021), 239–241
Linking options:
https://www.mathnet.ru/eng/mendc891
https://www.mathnet.ru/eng/mendc/v31/i2/p239
This publication is cited in the following 3 articles:
A. M. Gimazetdinov, V. V. Zagitov, Z. R. Makaev, N. S. Vostrikov, M. S. Miftakhov, “Some aspects of the synthesis and modification of cross-conjugated cyclopentenone prostaglandins”, Russ Chem Bull, 72:10 (2023), 2281
Airat M. Gimazetdinov, Aidar Z. Al'mukhametov, Mansur S. Miftakhov, “Development of a new approach for the synthesis of (+)-15-deoxy-Δ12,14-prostaglandin J2 methyl ester based on the [2+2]-cycloadduct of 5-trimethylsilylcyclopentadiene and dichloroketene”, New J. Chem., 46:14 (2022), 6708
A. Z. Al'mukhametov, G. V. Aralbaeva, A. M. Gimazetdinov, “Synthesis and Cytotoxic Properties of Cross-Conjugated Prostanoids with an exo-Methylidenecyclopentenone Fragment”, Russ J Org Chem, 58:11 (2022), 1589
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