ISSN:
1573-9171
Keywords:
9α-hydroxy-16α,17α-epoxypregnanes
;
16α,17α-isopropylidene derivatives of 9α-hydroxypregnanes and their thioanalogs
;
cis-cleavage of acetic and thioacetic acid
;
20-carboethoxyhydrazone of 16α,17α-epoxypregnane
Source:
Springer Online Journal Archives 1860-2000
Topics:
Chemistry and Pharmacology
Notes:
Abstract A study was carried out on the pathways for the transformation of 16α,17α-epoxypregn-4-ene-9α,21-diol-3,20-dione to give 16α,17α-isopropylidene derivatives of pregn-4-ene-9α,16α,17α,21-tetraol-3,20-dione and its 17α-thioanalog. The key step in this pathway is thecis-cleavage of the 20-carboethoxyhydrazone of this epoxide by acetic and thioacetic acids and subsequent condensation of the products formed with acetone. This pathway is an efficient approach to the synthesis of the 16α,17α-dioxolane derivative and is equally efficient for preparation of the thioanalog, namely, 16α,17α-isopropylidenepregn-4-ene-9α,16α,21-triol-17α-thiol-3,20-dione, which has already been synthesized by an alternative method.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1007/BF00863832
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