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Synlett 2003(2): 0219-0220
DOI: 10.1055/s-2003-36805
LETTER
© Georg Thieme Verlag Stuttgart · New York

First Synthesis of (±)-Pyricuol, a Plant Pathogen Isolated from Rice Blast Disease Fungus Magnaporthe grisea

Hiromasa Kiyota*, Rumi Ueda, Takayuki Oritani, Shigefumi Kuwahara
Department of Applied Bioorganic Chemistry, Division of Life Science, Graduate School of Agricultural Science, Tohoku University, 1-1 Tsutsumidori-Amamiyamachi, Aoba-ku. Sendai 981-8555, Japan
Fax: +81(22)7178783; e-Mail: kiyota@biochem.tohoku.ac.jp;
Further Information

Publication History

Received 8 November 2002
Publication Date:
22 January 2003 (online)

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Abstract

Pyricuol, a novel plant pathogen isolated from rice blast disease fungus Magnaporthe grisea, was synthesized as a racemate from 2,3-dimethylphenol using the [2,3]-Wittig rearrangement as the key step.

Key words

pyricuol - Magnaporthe grisea - [2,3]-Wittig rearrangement - total synthesis - natural products

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(±)-Pyricuol (4), a pale yellow oil. 1H NMR (500 MHz, CDCl3) δ = 1.76 (3 H, dd, J = 6.4, 1.5 Hz, 13-H), 3.15 (1 H, m, 10-H), 3.61 (1 H, m, 14-H), 3.63 (1 H, m, 14-H), 5.43 (1 H, ddq, J = 15.4, 7.8, 1.5 Hz, 11-H), 5.68 (1 H, ddq, J = 15.4, 0.5, 6.4 Hz, 12-H), 6.04 (1 H, dd, J = 15.6, 7.3 Hz, 9-H), 6.87 (1 H, d, J = 8.3 Hz, 6-H), 6.92 (1 H, d, J = 7.6 Hz, 4-H), 6.96 (1 H, d, J = 15.6 Hz, 8-H), 7.44 (1 H, t, J = 7.9 Hz, 5-H), 10.30 (1 H, s, CHO), 11.86 (1 H, s, OH). HRMS (EI): m/z calcd for C14H16O3: 232.1099; found: 232.1099.