Regioselective synthesis using the deuterium isotope effect
Journal Article
·
· J. Org. Chem.; (United States)
Dehydration of 1a by various procedures invariably produced more exo olefin 2a than endo olefin 3a. This could be reversed by introduction of deuterium in the Me-21 group of the starting material. Thus, dehydration of 1b could afford more endo olefin 3b than exo olefin 2b due to the deuterium isotope effect. A regioselective synthesis of 18-oxoprogesterone (15a) from 3..beta..-hydroxypregn-5-en-20-one (5a) was carried out taking advantage of the deuterium isotope effect as depicted in Scheme I. The key steps were dehydration of 7b to predominantly endo olefin 9b and removal of the deuteriums from 18-oxoprogesterone-17..cap alpha..,21,21,21-d/sub 4/ (15b) to give 15a.
- Research Organization:
- G.D. Searle and Co., Chicago, IL
- OSTI ID:
- 6417939
- Journal Information:
- J. Org. Chem.; (United States), Journal Name: J. Org. Chem.; (United States) Vol. 46:9; ISSN JOCEA
- Country of Publication:
- United States
- Language:
- English
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