Method of synthesizing forskolin from 9-deoxyforskolin

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

1988-01-25

1989-04-18

Chan, Nicky

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

549383, C07D40704, C07D31178

Patent

active

048228966

ABSTRACT:
A method of regioselectively and stereoselectively synthesizing forskolin (8,13-epoxy-1.alpha.,6.beta.,7.beta.,9.alpha.-tetrahydroxy-labd-14-en-11-o ne) 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.-trihydroxy-lab d-14-ene-6,7-carbonate and 11,12-dehydro-8,13-epoxy-11-methoxy-1.alpha.,6.beta.,7.beta., 9.alpha.-tetrahydroxylabd-14-end-6,7-carbonate and the corresponding dimethyl acetal compounds are believed to be novel.

REFERENCES:
Anderson et al., JACS, 76, 743 (1954).

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