Method for the preparation of (+)-calanolide A and intermediates

Details Method for the preparation of (+)-calanolide A and intermediates Method for the preparation of (+)-calanolide A and intermediates

1994-08-03

1996-02-06

Ivy, C. Warren

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

549282, 549289, C07D31178, C07D31176

Patent

active

054896975

ABSTRACT:
A method for preparing (.+-.)-calanolide A, 1, a potent HIV reverse transcriptase inhibitor, from chromene 4 is provided. Useful intermediates for preparing (.+-.)-calanolide A and its derivatives are also provided.
According to the disclosed method, chromene 4 intermediate was reacted with acetaldehyde diethyl acetal in the presence of an acid catalyst with heating to produce chromanone 7. Reduction of chromene 7 with sodium borohydride, in the presence of cerium trichloride, produced (.+-.)-calanolide A, which was purified chromatographically.

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