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Synthesis and Absolute Configuration of (−)‐Phytocassane D, a Diterpene Phytoalexin Isolated from the Rice Plant, Oryza sativa
Author(s) -
Yajima Arata,
Mori Kenji
Publication year - 2000
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200012)2000:24<4079::aid-ejoc4079>3.0.co;2-r
Subject(s) - absolute configuration , diterpene , phytoalexin , chemistry , stereochemistry , oryza sativa , absolute (philosophy) , ketone , organic chemistry , biochemistry , gene , resveratrol , philosophy , epistemology
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.