Diastereoselective Synthesis of an Isoprostane: (±)-8-epi-PGF2α Ethyl Ester
- 1 January 1997
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 62 (1) , 194-198
- https://doi.org/10.1021/jo9616365
Abstract
A total synthesis of the isoprostane (+/-)-8-epi-PGF(2)(alpha) ethyl ester (5) is described, based on the diastereoselective cyclization of alpha-diazo ketone 7. This ketone is assembled by aldol condensation between alpha-diazo ketone 8 and aldehyde 9. The sequential alpha-diazo ketone aldol/insertion described here offers a powerful new approach to cycloalkane construction.Keywords
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