Method of synthesizing forskolin from 9-deoxyforskolin

Details Method of synthesizing forskolin from 9-deoxyforskolin Method of synthesizing forskolin from 9-deoxyforskolin

1989-11-24

1991-04-16

Shen, Cecilia

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

549229, 549389, C07D31192

Patent

active

050084070

ABSTRACT:
A method of regioselectively and stereoselectively synthesizing forskolin (8,13-epoxy-1.alpha.,6.beta.,7.beta.,9.alpha.-tetrahydroxylabd-14-en-11-on e) from 9-deoxyforskolin (8,13-epoxy-1.alpha.,6.beta.,7.beta.-trihydroxylabd-14-en-11-one) with a good yield is described. In a preferred embodiment, it comprises an enol ether formation from 8,13-epoxy-1.alpha.,6.beta.,7.beta.-trihydroxylabd-14-en-11-one-6,7-carbon ate, oxidation of the enol ether with a suitable peroxy acid to obtain 11,12-dehydro-8,13-epoxy-11-methoxy-1.alpha.,6.beta.,7.beta.,9.alpha.-tetr ahydrolabd-14-ene-6,7-carbonate and hydrolysis of the latter under an acidic condition to obtain 8,13-epoxy-1.alpha.,6.beta.,7.beta.,9.alpha.-tetrahydroxylabd-14-en-11-one -6,7-carbonate. As an alternative way of protecting the two hydroxy groups at carbon-6 and carbon-7, they may also be converted to dimethyl acetal during the synthetic sequence. Four compounds produced in the synthetic scheme as intermediates, namely, 9,11-dehydro-8,13-epoxy-11-methoxy-1.alpha.,6.beta.,7.beta.-trihydroxylabd -14-ene-6,7-carbonate and 11,12-dehydro-8,13-epoxy-11-methoxy-1.alpha.,6.beta.,7.beta.,9.alpha.-tetr ahydroxylabd-14-ene-6,7-carbonate and the corresponding dimethyl acetal compounds are believed to be novel.

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