Subscribe to RSS
DOI: 10.1055/s-2003-36805
First Synthesis of (±)-Pyricuol, a Plant Pathogen Isolated from Rice Blast Disease Fungus Magnaporthe grisea
Publication History
Publication Date:
22 January 2003 (online)
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
- 1
Umetsu N.Kaji J.Tamari K. Agric. Biol. Chem. 1972, 36: 859 ; and references cited therein - 2
Iwasaki S.Nozoe S.Okuda S.Sato Z.Kozawa T. Tetrahedron Lett. 1969, 3977 - 3
Nukina M.Otuki T.Kurebayashi T.Hosokawa K.Sekine M.Ito S.Suenaga M.Sato A.Sassa T. Abstract from 38th Symposium on the Chemistry of Natural Products Sendai; Japan: 1996. p.391 - 4
Nukina M.Ikeda M.Umezawa T.Tasaki H. Agric. Biol. Chem. 1981, 45: 2161 -
5a
Suzuki M.Sugiyama T.Watanabe M.Yamashita K. Agric. Biol. Chem. 1986, 50: 2159 ; and a reference cited therein -
5b
Suzuki M.Sugiyama T.Watanabe M.Murayama T.Yamashita K. Agric. Biol. Chem. 1987, 51: 1121 - 6
Kim J.-C.Min J.-Y.Kim H.-T.Cho K.-Y.Yu S.-H. Biosci. Biotechnol. Biochem. 1998, 62: 173 -
7a
Still WC.Mitra A. J. Am. Chem. Soc. 1978, 100: 1927 -
7b For a recent review of
the [2,3]-Wittig rearrangement, see:
Nakai T.Mikami K. Org. React. 1994, 46: 105 - 8
Sugiyama T.Watanabe M.Sassa T.Yamashita K. Agric. Biol. Chem. 1983, 47: 2411 - 9
Nicolaou KC.Vassilicogiannakis G.Montagnon D. Angew. Chem. Int. Ed. 2002, 41: 3276 - 10
Michel P.Gennin D.Rassat A. Tetrahedron Lett. 1999, 40: 8575 - 11
Seyferth D.Andrews BS. J. Organomet. Chem. 1971, 30: 151
References
(±)-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.