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

Yajima Arata | Zendy; Mori Kenji | Zendy

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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.

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