Journal of the American Chemical Society p. 337 - 342 (1980)
Update date:2022-07-29
Topics:
Bartlett, Paul A.
Adams, Jerry L.
A total synthesis of racemic Prelog-Djerassi lactone (1) has been achieved using the mercuric ion induced cyclization of aldehyde acid 12a to control the stereochemistry at C-2 and C-3.Demercuration of the product (14a) is selectively accomplished with sodium trithiocarbonate in methanol at -60 deg C, affording the Prelog-Djerassi lactone (1) and the 2-epi isomer 17 in 3.5:1 ratio after hydrolysis and oxidation.Demercuration with sodium borohydride, hydrolysis, and oxidation result in the 2-epi compound 17 almost exclusively.
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