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Title:
PRODUCTION OF 3-BETA, 14-BETA-DIHYDROXYETHIANALDEHYDE
Document Type and Number:
Japanese Patent JPH07316189
Kind Code:
A
Abstract:

PURPOSE: To efficiently obtain the subject new compound usable as a raw material for anti-hypertensive agents by oxidizing and then reducing the unsaturated lactone ring of digitoxigenin-3-acetate with a periodate in the presence of ruthenium tetroxide followed by hydrolyzing and then oxidizing the resulting product.

CONSTITUTION: First, the α,β-unsaturated lactone ring of digitoxigenin-3-acetate of formula I (Ac is acetyl) is oxidized with an alkali metal periodate in the presence of a catalytic amount of ruthenium tetroxide to form a keto derivative of formula II [R is H, COCHO, COCH(OH)2 or COCOOH]. Secondly, the keto derivative is reduced with sodium borohydride followed by hydrolyzing the 3- and 21-sites of the ester group to form the corresponding tetrol of formula III. Subsequently, the tetrol is oxidized with an alkali metal periodate to efficiently obtain the objective 3β-14β-dihydroxyethianaldehyde of formula IV useful as an intermediate for producing anti-hypertensive agents.


Inventors:
MAURO GOTSUBIINI
MARUKO TOTSURI
Application Number:
JP12361295A
Publication Date:
December 05, 1995
Filing Date:
May 23, 1995
Export Citation:
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Assignee:
SIGMA TAU IND FARMACEUTI
International Classes:
B01J23/46; C07B61/00; C07J3/00; C07J5/00; C07J15/00; C07J19/00; C07J71/00; C07J75/00; (IPC1-7): C07J75/00; B01J23/46; C07J3/00
Attorney, Agent or Firm:
Aoyama Ryo (1 person outside)



 
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