References
1a
Rinehart KL.
Holt TG.
Fregeau NL.
Stroh JG.
Shield LS.
Seigler DS.
J. Nat. Prod.
1990,
53:
771
1b
Wright AE.
Forleo DA.
Gunawardana GP.
Gunasekera SP.
Koehn FE.
McConnell OJ.
J. Org. Chem.
1990,
55:
4508
1c
Suwanborirux K.
Charupant K.
Amnuoypol S.
Pummangura S.
Kubo A.
Saito N.
J. Nat. Prod.
2002,
65:
935
2a
Ikeda Y.
Shimada Y.
Honjo K.
Okumoto T.
Munakata T.
J. Antibiot.
1983,
36:
1290
2b
Saito N.
Harada S.
Yamashita M.
Saito T.
Yamaguchi Y.
Kubo A.
Tetrahedron
1995,
51:
8213
3 For a recent review, see: Scott JD.
Williams RM.
Chem. Rev.
2002,
102:
1669
4a
Corey EJ.
Gin DY.
Kania RS.
J. Am. Chem. Soc.
1996,
118:
9202
4b
Corey EJ.
Gin DY.
Tetrahedron Lett.
1996,
37:
7163
5a
Endo A.
Yanagisawa A.
Abe M.
Tohma S.
Kan T.
Fukuyama T.
J. Am. Chem. Soc.
2002,
124:
2545
5b
Endo A.
Kann T.
Fukuyama T.
Synlett
1999,
7:
1103
6
Cuevas C.
Pérez M.
Martin MJ.
Chicharro JL.
Fernandez-Rivas C.
Flores M.
Francesch A.
Gallego P.
Zarzuelo M.
De La Calle F.
Garcia J.
Polanco C.
Rodriguez I.
Manzanares I.
Org. Lett.
2000,
2:
2545
7a
Saito N.
Kamayachi H.
Tachi M.
Kubo A.
Heterocycles
1999,
51:
9
7b
Saito N.
Tachi M.
Seki R.
Kamayachi H.
Kubo A.
Chem. Pharm. Bull.
2000,
48:
1549
8a
Zhou B.
Edmondson S.
Padron J.
Danishefsky SJ.
Tetrahedron Lett.
2000,
41:
2039
8b
Zhou B.
Guo J.
Danishefsky SJ.
Tetrahedron Lett.
2000,
41:
2043
8c
Zhou B.
Guo J.
Danishefsky SJ.
Org. Lett.
2002,
4:
43
9a
Jin W.
Williams RM.
Tetrahedron Lett.
2003,
44:
4635
9b
Jin W.
Metobo S.
Williams RM.
Org. Lett.
2003,
5:
2095
10
De Paolis M.
Chiaroni A.
Zhu J.
Chem. Commun.
2003,
2896
11
Corey EJ.
Xu F.
Noe MC.
J. Am. Chem. Soc.
1997,
119:
12414
12
Lygo B.
Wainwright PG.
Tetrahedron Lett.
1997,
38:
8595
13 For an earlier contribution, see: O’Donnell MJ.
Bennett WD.
J. Am. Chem. Soc.
1989,
111:
2353
14
Sinhababu AK.
Gosh AK.
Borchardt RT.
J. Med. Chem.
1985,
28:
1273
15 Compound 6. [α]D
23 +13 (c = 0.8, CHCl3). IR (CHCl3): 3382, 3034, 2981, 2938, 1725, 1598, 1495, 1370, 1293, 1218, 1178 cm-1. 1H NMR (250 MHz, CDCl3, 293 K): δ = 7.76 (d, J = 7.6 Hz, 2 H), 7.32 (d, J = 7.5 Hz, 2 H), 6.90 (br s, 1 H), 6.79 (br s, 1 H), 3.67 (s, 3 H), 3.48 (dd, J = 7.3, 5.5 Hz, 1 H), 2.88 (dd, J = 13.7, 5.5 Hz, 1 H), 2.67 (dd, J = 13.7, 7.3 Hz, 1 H), 2.44 (s, 3 H), 2.19 (s, 3 H), 1.42 (s, 9 H). 13C NMR (75 MHz, CDCl3, 293 K): 174.0, 149.3, 145.1, 142.2, 133.1, 132.8, 130.4, 129.5, 129.2, 128.5, 128.4, 121.8, 81.2, 60.5, 56.0, 40.2, 28.1, 27.9, 21.6, 15.9. MS (ESI+): m/z = 436.2 [M + H]+, 458.3 [M + Na]+, 474.2 [M + K]+. HRMS (ESI+): m/z [M + H+] calcd for C22H30O6S: 436.1794; found: 436.1789.
Compound 7. [α]D
23 +22 (c = 1, CHCl3). IR (CHCl3): 3426, 3024, 2933, 2830, 1716, 1590, 1496, 1343, 1232, 1087, 1007 cm-1. 1H NMR (300 MHz, CDCl3, 293 K): 9.52 (s, 1 H), 6.56 (m, 2 H), 5.96 (ddd, J = 17.7, 12.5, 7.2 Hz, 1 H), 5.82 (m, 1 H), 5.33 (ddt, J = 16.8, 1.7, 1.6 Hz, 1 H), 5.17 (m, 4 H), 4.47 (m, 4 H), 4.46 (m, 1 H), 3.80 (s, 3 H), 2.98 (dd, J = 14.0, 6.5 Hz, 1 H), 2.89 (dd, J = 14.0, 6.8 Hz, 1 H), 2.21 (s, 3 H). 13C NMR (75 MHz, CDCl3, 293 K): 199.2, 155.8, 151.6, 146.7, 133.2, 132.5, 132.3, 130.6, 123.8, 118.0, 117.5, 112.7, 69.4, 65.9, 60.9, 60.1, 35.2, 15.9. MS (ESI+): m/z = 334.2 [M + H]+.
16a
Trost BM.
Bunt RC.
Pulley SR.
J. Org. Chem.
1994,
59:
4202
16b
Helmchen G.
Sauber K.
Tetrahedron Lett.
1972,
3873