Abstract:
The title compound, as the new chiral building block for bioactive cyclopentenones, was prepared in 8 steps with 15% overall yield. The key steps involve selective homologation in intermediate [(1S,2R,5R)-5-trimethysilylcyclopent-3-ene- 1,2-diyl]dimethanol by regioselective silylation followed by oxidation and the Wittig reaction.
Citation:
A. Z. Al'mukhametov, A. M. Gimazetdinov, M. S. Miftakhov, “A convenient synthesis of enantiopure (4aS,7aR)-1,4,4a,7a-tetrahydrocyclopenta[c]pyran-3,7-dione”, Mendeleev Commun., 30:1 (2020), 10–11
Linking options:
https://www.mathnet.ru/eng/mendc1084
https://www.mathnet.ru/eng/mendc/v30/i1/p10
This publication is cited in the following 4 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
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
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