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A convenient synthesis of enantiopure (4aS,7aR)-1,4,4a,7a-tetrahydrocyclopenta[c]pyran-3,7-dione

Aidar Zufarovich Al'mukhametov 1
Aidar Zufarovich Al'mukhametov
, 
Airat Maratovich Gimazetdinov 1
Airat Maratovich Gimazetdinov
, 
Mansur Sagar'yarovich Miftakhov 1
Mansur Sagar'yarovich Miftakhov
10.1016/j.mencom.2020.01.003
Published 2019-12-30
Communication , Volume 30, Issue 1, 10-11
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Al'mukhametov A. Z., Gimazetdinov A. M., Miftakhov M. S. A convenient synthesis of enantiopure (4aS,7aR)-1,4,4a,7a-tetrahydrocyclopenta[c]pyran-3,7-dione // Mendeleev Communications. 2019. Vol. 30. No. 1. pp. 10-11.
GOST all authors (up to 50) Copy
Al'mukhametov A. Z., Gimazetdinov A. M., Miftakhov M. S. A convenient synthesis of enantiopure (4aS,7aR)-1,4,4a,7a-tetrahydrocyclopenta[c]pyran-3,7-dione // Mendeleev Communications. 2019. Vol. 30. No. 1. pp. 10-11.
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TY - JOUR
DO - 10.1016/j.mencom.2020.01.003
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2020.01.003
TI - A convenient synthesis of enantiopure (4aS,7aR)-1,4,4a,7a-tetrahydrocyclopenta[c]pyran-3,7-dione
T2 - Mendeleev Communications
AU - Al'mukhametov, Aidar Zufarovich
AU - Gimazetdinov, Airat Maratovich
AU - Miftakhov, Mansur Sagar'yarovich
PY - 2019
DA - 2019/12/30
PB - Mendeleev Communications
SP - 10-11
IS - 1
VL - 30
ER -
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@article{2019_Al'mukhametov,
author = {Aidar Zufarovich Al'mukhametov and Airat Maratovich Gimazetdinov and Mansur Sagar'yarovich Miftakhov},
title = {A convenient synthesis of enantiopure (4aS,7aR)-1,4,4a,7a-tetrahydrocyclopenta[c]pyran-3,7-dione},
journal = {Mendeleev Communications},
year = {2019},
volume = {30},
publisher = {Mendeleev Communications},
month = {Dec},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2020.01.003},
number = {1},
pages = {10--11},
doi = {10.1016/j.mencom.2020.01.003}
}
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Al'mukhametov, Aidar Zufarovich, et al. “A convenient synthesis of enantiopure (4aS,7aR)-1,4,4a,7a-tetrahydrocyclopenta[c]pyran-3,7-dione.” Mendeleev Communications, vol. 30, no. 1, Dec. 2019, pp. 10-11. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2020.01.003.

Keywords

allylsilanes
asymmetric synthesis
bicyclic δ-lactones
bioactive compounds
cyclopentanoids
cyclopentenones
epoxidation
ion-exchange resins.
lactonization
silylation

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.

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