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Synthesis and Absolute Configuration of (−)-Phytocassane D, a Diterpene Phytoalexin Isolated from the Rice Plant,Oryza sativa

2000; Wiley; Volume: 2000; Issue: 24 Linguagem: Inglês

10.1002/1099-0690(200012)2000

1434-193X

Arata Yajima, Kenji Mori,

Natural product bioactivities and synthesis

To determine the absolute configuration of the phytocassane group of phytoalexins, the naturally occurring (−)-phytocassane D was synthesized from the (R)-Wieland−Miescher ketone, in an approach based on the preliminary model synthesis of the unnatural (+)-2-deoxyphytocassane A. By comparison of their CD spectra with those of synthetic phytocassanes of known absolute configuration, phytocassanes A−E were shown to possess the ent-cassane skeleton.