Synthesis of NH006 - A photostable fungicide effective against Botrytis cinerea - According to the asymmetric total synthesis of MK8383

Nobuyuki Hayashi, Kentaro Yamamoto, Nobuto Minowa, Masaaki Mitomi, Masahisa Nakada

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

MK8383, isolated from Phoma sp. T2526 in 1993, exhibits potent antibiotic activities against a variety of phytopathogens and has been considered a promising fungicide against Botrytis cinerea. Unfortunately, MK8383 is a photosensitive compound and it undergoes irreversible decomposition. Although much effort has been devoted to improving the photostability of MK8383 by chemical modification of its structure by a research group organized by Meiji Seika Kaishya, Ltd. and Mitsubishi Chemical Corporation, a photostable MK8383 derivative has never been prepared. We have found that a C13-14 double bond of MK8383 and (+)-phomopsidin is responsible for the photosensitivity, and herein, we report the synthesis of NH006, an MK8383 derivative with a saturated C13-14 double bond and (S) configuration at C14, based on the asymmetric total synthesis of MK8383. NH006 exhibits good photostability and potent antifungal activity against B. cinerea.

Original languageEnglish
Pages (from-to)1821-1825
Number of pages5
JournalOrganic and Biomolecular Chemistry
Volume8
Issue number8
DOIs
Publication statusPublished - 2010 Apr 7

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Fingerprint Dive into the research topics of 'Synthesis of NH006 - A photostable fungicide effective against Botrytis cinerea - According to the asymmetric total synthesis of MK8383'. Together they form a unique fingerprint.

  • Cite this