Synthesis and biological evaluation of bilobol and adipostatin A.

Ayano Tanaka, Yasuhiro Arai, Su-Nam Kim, Jungyeob Ham, Toyonobu Usuki

Index: J. Asian Nat. Prod. Res. 13(4) , 290-6, (2011)

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Abstract

Concise total synthesis of bilobol 5-pentadecenylresorcinol (1), isolated from Gingko biloba fruits, has been achieved in 10 steps with 51% overall yield from 3,5-dihydroxybenzoic acid (3). Adipostatin A (2), isolated from the fruits as well as from Streptomyces cyaneus 2299-SV1, has also been synthesized in two steps from methylated bilobol (10). The structure-activity relationship study of synthetic products was described by means of cytotoxic assay against human KB carcinoma cell lines.