Method of synthesizing forskolin from 9-deoxyforskolin

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

1989-01-25

1990-01-30

Chan, Nicky

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

549383, C07D31178, C07D40704

Patent

active

048974960

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-11-one-6,7-c arbonate. 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.-trihydroxylab- 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.

REFERENCES:
Anderson et al., JACS, 76, 743, (1954).
Ercoli et al., JACS, 75, 650, (1953).
Vedejs, JACS, 96, 5944, (1974).
House, "Modern Synthetic Reactions", 2nd Ed., Benjamin, Menlo Park, Calif., 1972, pp. 296-321.

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