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Total synthesis of the novel angiogenesis inhibitors epoxyquinols A and B

โœ Scribed by Goverdhan Mehta; Kabirul Islam


Book ID
104253426
Publisher
Elsevier Science
Year
2003
Tongue
French
Weight
451 KB
Volume
44
Category
Article
ISSN
0040-4039

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โœฆ Synopsis


The synthesis of the recently discovered angiogenesis inhibitors epoxyquinols A and B, having novel polyketide derived dimeric structures, has been accomplished from the readily available Diels-Alder adduct of cyclopentadiene and p-benzoquinone through a short, simple and flexible strategy that is diversity oriented and can be adapted to an asymmetric variant.


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A practical total synthesis of both enantiomers of epoxyquinols A and B has been developed. Key reactions are the chromatography-free preparation of an iodolactone by using acryloyl chloride as dienophile in the Diels-Alder reaction of furan, the lipase-mediated kinetic resolution of a cyclohexenol