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Phorbol Rearrangements
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DOI：10.1021/acs.jnatprod.8b00607.png)
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Abstract
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An alternative procedure for isolation of 4 beta-phorbol from seeds of Croton tiglium has been developed, and an artifact containing a furan ring formed by rearrangement of 12,13,20-O-triacylated phorbol derivatives into (6bS,7R,8R,8aS)-2-(hydroxymethyl)-5,7,9,9-tetramethyl-3,7,8,9,9a,9b-hexahydrocyclopropa[3',4']benzo[1',2':3,4]cyclohepta[1,2-b]furan-6b,8,8a-triol (8a) has been characterized. A mechanism involving an oxidative rearrangement and a decarboxylation for formation of the artifact is proposed.
Keywords:
PROTEIN-KINASE-C
CROTON-OIL
ESTERS
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