References
- 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
12 (±)-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.
