Abstract:
Synthetically useful chiral building blocks (3aS,6aR)-1,3,3a,6atetrahydro-4H-cyclopenta[c]furan-4-one and (3aS,6aR)-3a,6a-dihydro-1H-cyclopenta[c]furan-1,4(3H)-dione have been synthesized via a key allylsilane–allyl alcohol fragmentation pathway using (3aS,6S,6aR)-6-(trimethylsilyl)-3,3a,6,6a-tetrahydro-1H-cyclopenta[c]furan-1-one as an illustrative example.
Citation:
A. Z. Al'mukhametov, A. M. Gimazetdinov, M. S. Miftakhov, “Synthetically attractive chiral cyclopentenone building blocks conjugated with tetrahydro- and 2-oxotetrahydrofurans”, Mendeleev Commun., 28:4 (2018), 362–363
Linking options:
https://www.mathnet.ru/eng/mendc1766
https://www.mathnet.ru/eng/mendc/v28/i4/p362
This publication is cited in the following 5 articles:
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
V. V. Loza, Z. R. Valiullina, M. S. Miftakhov, “Adducts of dichloroketene with 1,3-cyclopentadienes in the synthesis of bioactive cyclopentanoids”, Russ Chem Bull, 70:1 (2021), 1
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
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
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