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A Novel Scheme for the Synthesis of 21-Acetoxypregna-1,4,9(11)-triene- 17α,21-diol-3,20-dione from 9α-Hydroxyandrostenedione

Author(s):

Nguyen Thi Diep* and Luu Duc Huy   Pages 1 - 5 ( 5 )

Abstract:


Background: Vietnam currently imports the pharmaceutical compounds up to 90%, in particular 100% of steroidal drug. 21-Acetoxypregna-1,4,9(11)-triene-17α,21-diol-3,20-dione is considered key intermediate in the steroidal drug synthesis scheme. In the previous synthetic strategies of corticoids, introducing double bond in the 1(2)-position of steroid molecular was usually performed at the final stage with poor yield, therefore, to decline in economic efficiency.

Objective: Study and development of novel and effective methods for synthesis of 21-Acetoxypregna-1,4,9(11)-triene-17α,21-diol-3,20-dione.

Method: Acetylene method for construction of pregnane side chain, introduction of Δ1(2)-double bond, epimerization, Stork’s iodination procedure.

Result: From 9α-hydroxyandrostenedione, 21-acetoxypregna-1,4,9(11)-triene-17α,21-diol-3,20-dione was prepared with good yield.

Conclusion: The introduction of double bond in the 1(2)-position was carried out in advance to have increased the economic efficiency of the entire process. 21-Acetoxypregna-1,4,9(11)-triene-17α,21-diol-3,20-dione has been synthesized from 9α-hydroxyandrostendion based on an novel, effective and feasible scheme. For the first time, the indirect epimerization mechanism has been further clarified and the configuration of C-17 center of the received product has also been further confirmed by NOESY data.

Keywords:

phytosterols, 9α-hydroxyandrostenedione, 21-acetoxypregna-1 & 4 & 9(11)-triene-17? & 21-diol-3 & 20-dione, steroid, corticoid, NOESY.

Affiliation:

Institute of Chemistry, Vietnam Academy of Science and Technology, Hanoi, Institute of Chemistry, Vietnam Academy of Science and Technology, Hanoi



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