ꢀꢁꢍꢉ
N. Defacqz et al.
3$3(5
ꢉꢈꢎꢅ'L>ꢊGLHWK\OꢋSKRVSKRQR@DQLOLQHꢄꢊꢇDꢋꢄ
(8) Varvoglis, A. G. UrꢁhurqꢁꢀGrꢃ ꢀꢇꢍꢉ, 31.
(9) Liu, Z.-D.; Chen, Z.-C. Turvꢀꢀꢇꢇꢁ, 373.
(10) Yang, G. Eꢃꢀ6ꢃꢀ8urꢃꢀTp. ꢀꢇꢇꢂ, ', 5883.
(11) Grummitt, O.; Vourlogianes, N.; Mehaffey, J.; Tebbe, R. Pꢁtꢃꢀ
QꢁrꢃꢀQꢁp. ꢀꢇꢍꢏ, !, 5.
Compound ꢇD was prepared from ꢎD (0.3 g, 1.195 mmol). Chroma-
tography with hexane/EtOAc (from 70:30 to 30:70) gave 0.101 g of
pure ꢇD (23%) as a colourless oil; Rf (silica gel, hexane/EtOAc,
30:70) 0.20.
(12) Golubski, Z. E.; Skrowaczewska, Z. Turv ꢀꢇꢍꢇ, 21.
(13) Yasui, S.; Fujii, M.; Kawano, C.; Nishimura, K.; Shioji, K.;
Ohno, A. Eꢃꢀ8urꢃꢀTpꢃꢀQrꢁxvꢀUꢁhꢃꢀ! ꢀꢇꢇꢎ, 177.
(14) Kargin, Y. M.; Nikitin, E. V.; Parakin, O. V.; Romanov, G. V.;
Pudovik, A. N. QuuꢁꢀTysꢁ ꢀꢇꢃꢏ, ', 55.
(15) Effenberger, F.; Kottmann, H. Urꢁhurqꢁꢀꢀꢇꢃꢌ,ꢀ# , 4171.
(16) Kottmann, H.; Skarzewski, J.; Effenberger, F. Turv ꢀꢇꢃꢍ,
797.
(17) Jardine, A. M.; Vather, S. M. EꢃꢀPꢁtꢃꢀ8urꢃ ꢀꢇꢃꢃ, $", 3983.
(18) Bennett, S. N. L.; Hall, R. G. Eꢃꢀ8urꢃꢀTpꢃꢀQrꢁxvꢀUꢁhꢃꢀ
ꢀꢇꢇꢌ, 1145.
(19) Masson, S.; Saint-Clair, J.-F., Dore, A.; Saquet, M.ꢀ7yyꢃꢀTpꢃꢀ
8uvꢃꢀAꢁꢃꢄꢀꢇꢇꢂ, "", 951.
(20) Plumb, J. B.; Obrycki, R.; Griffin, C. E. EꢃꢀPꢁtꢃꢀ8urꢃ ꢀꢇꢂꢌ,
" , 2455.
(21) Bunnett, J. F.; Creary, X. EꢃꢀPꢁtꢃꢀ8urꢃ ꢀꢇꢍꢎ, "(, 3612.
(22) Hoz, S.; Bunnett, J. F. Eꢃꢀ6ꢃꢀ8urꢃꢀTpꢃ ꢀꢇꢍꢍ, ((, 4690.
(23) Bard, R. R.; Bunnett, J. F., Traber, R. P. EꢃꢀPꢁtꢃꢀ8urꢃ ꢀꢇꢍꢇ,
##, 4918.
IR (film): n = 3412, 3326, 3218, 2984, 1635, 1600, 1495, 1445,
1393, 1230, 1162, 1098, 1024, 965 cm–1.
MS(FAB): / = 366 (M+ + 1).
Anal. calcd for C14H25NO6P2: C, 46.03; H, 6.90; N, 3.83. Found C,
46.05; H, 6.78; N, 3.44.
ꢉꢈꢂꢅ'L>ꢊGLHWK\OꢋSKRVSKRQR@DQLOLQHꢄꢊꢇEꢋ
Compound ꢇE was prepared from ꢎE (0.5 g, 1.933 mmol). Chroma-
tography on basic alumina with hexane/EtOAc (from 70:30 to
0:100) gave a pure fraction of ꢇE (0.105g, 15%) as a colourless oil;
Rf (silica gel, EtOAc) 0.35.
IR (film): n = 3421 (br), 2984, 1614, 1565, 1441, 1393, 1222, 1019,
967, 817 cm–1.
MS(EI): / = 365 (M+), 337, 309, 256, 228.
Anal. calcd for C14H25NO6P2: C, 46.03; H, 6.90; N, 3.83. Found C,
46.46; H, 6.93; N, 3.53.
(24) Galli, C., Bunnett, J. F. Eꢃꢀ6ꢃꢀ8urꢃꢀTpꢃ ꢀꢇꢃꢀ, ꢄ"ꢅ 7140.
(25) Bunnett, J. F.; Mitchel, E. Urꢁhurqꢁꢀꢀꢇꢃꢌ,ꢀ# , 4119.
(26) Bulot, J. J.; Aboujaoude, E. E., Collignon, N., Savignac, P.
QuuꢁꢀhqꢀTysꢁ ꢀꢇꢃꢎ, ! , 197.
(27) Beugelmans, R., Chbani, M. IrꢀEꢃꢀ8urꢃꢀꢀꢇꢇꢎ, ', 949.
(28) Obrycki, R., Griffin, C. E. EꢃꢀPꢁtꢃꢀ8urꢃ ꢀꢇꢂꢃ, "", 632.
(29) Ziegler Jr., C. B.; Heck, R. F. EꢃꢀPꢁtꢃꢀ8urꢃ ꢀꢇꢍꢃ, 641.
(30) Issleib, K., Vollmer, R. aꢃꢀ8urꢃ ꢀꢇꢍꢃ, ', 451.
(31) Bunnett, J. F. Urꢁhurqꢁ ꢀꢇꢇꢁ, #(, 4477.
(32) Denney, D. B.; Denney, D. Z. Urꢁhurqꢁ ꢀꢇꢇꢀ, #&, 6577.
(33) Galli, C.; Gentili, P. Eꢃꢀ8urꢃꢀTpꢃꢅꢀQrꢁxvꢀUꢁhꢃꢀ! ꢀꢇꢇꢁ,
1135.
$FNQRZOHGJHPHQW
This work was generously supported by the Fonds de la Recherche
Scientifique (FNRS, Belgium), the Fonds du Développement Sci-
entifique (FDS, UCL, Belgium), and the Institut de recherches Ser-
vier (France). We thank Valèrie Verbois and Olivier Gaziaux for
technical assistance.
5HIHUHQFHV
(1) Tavs, P. 8urꢃꢀ7rꢁꢃ ꢀꢇꢍꢏ, ꢄ", 2428.
(2) Grabiak, R. C.; Miles, J. A.; Schwenzer, G. M. Quuꢁꢀ
Tysꢁꢀꢀꢇꢃꢏꢈ (, 197.
(3) Balthazor, T. M.; Grabiak, R. C. EꢃꢀPꢁtꢃꢀ8urꢃꢀꢀꢇꢃꢏ, #$,
5425.
(4) Tavs, P.; Korte, F. Urꢁhurqꢁn ꢀꢇꢂꢍ, !", 4677.
(5) Osuka, A.; Ohmasa, N.; Yoshida, Y.; Suzuki, H. Turvꢀ
ꢀꢇꢃꢁ, 69.
(34) Bunnett, J. F. 6ppꢃꢀ8urꢃꢀSrꢃ ꢀꢇꢇꢉ, !$, 2.
(35) Tomaselli, G. A.; Bunnett, J. F. EꢃꢀPꢁtꢃꢀ8urꢃ ꢀꢇꢇꢉ, $&, 2710.
(36) Bolton R., Moore C.; Sandall, J. P. B.ꢀEꢃꢀ8urꢃꢀTpꢃꢅꢀQrꢁxvꢀ
Uꢁhꢃꢀ! ꢀꢇꢃꢉ, 1593.
Article Identifier:
1437-210X,E;1999,0,08,1368,1372,ftx,en;P00399SS.pdf
(6) Hirao, T.; Masunaga, T.; Yamada, N.; Ohshiro, Y.; Agawa, T.
7yyꢀ8urꢃꢀTpꢃꢀEꢃ ꢀꢇꢃꢉ, $$, 909.
(7) Lu, X.; Zhu, J. Turv ꢀꢇꢃꢍ, 726.
Synthesis 1999, No. 8, 1368–1372 ISSN 0039-7881 © Thieme Stuttgart · New York