Investigations on the chemistry of berbanes. 10. Synthesis of raunescinone analogs with hypotensive and antihypertensive activity

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Abstract
The pharmacologically active (methylenedioxy)- and diethoxyepialloberbane keto esters were synthesized with use of the readily available keto esters as starting material. By choice of the appropiate reaction sequence both antipodes of keto ester can be employed to provide any enantiomer of the desired raunescinone analog 1a [(1R, 12S, 17S)-methyl 7,8-(methylenedioxy)-14-oxo-15-[(3,4,5-trimethoxybenzoyl)oxy]-13-epialloberbanecarboxylate]. Hypotensive, antihypertensive and central depressant effects of 1a are described in rats and mice. The principal effect observed for 1a was a potent hypotensive and antihypertensive effect of long duration without depression of the CNS.