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SYNLETT
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corresponding α-hydroxyketone (95%) (m.p. = 52-53 °C) which was
Iwadare, H.; Sakoh, H.; Tani, Y.; Hasegawa, M.; Saitoh, K. Proc.
Japan Acad., 1997, 73, 95.
then treated with vinylmagnesium bromide so as to effect a ligand
20
assisted nucleophilic addition (LANA) reaction. In this way a ca. 10:1
3.
Martin, S. F.; Assercq, J.-M.; Austin, R. E.; Dantanarayana, A. P.;
Fishpaugh, J. R.; Gluchowski, C.; Guinn, D. E.; Hartmann, M.;
Tanaka, T.; Wagner, R.; White, J. B. Tetrahedron, 1995, 51, 3455.
mixture 30 and 5-epi-30 was obtained (55% combined yield). The
mono-benzyl ether 31 (53%) of diol 30 underwent smooth anionic oxy-
Cope rearrangement upon treatment with KH/18-C-6 at 0-18 °C and
after quenching the enolate anion 32 so-formed with saturated aqueous
4.
5.
Paquette, L. A. Tetrahedron, 1997, 53, 13971.
Almqvist, F.; Ekman, N.; Frejd, T. J. Org. Chem., 1996, 61, 3794
and references cited therein.
ammonium chloride the bicyclo[5.3.1]undecenone 33 (47%) {[α]
=
D
+38° (c 0.7 in CHCl at 20 °C)}, which embodies the AB-ring system
3
6.
For a review on the applications of cis-1,2-dihydrocatechols in
synthesis see Hudlicky, T.; Thorpe, A. J. Chem. Commun. 1996,
1993.
associated with taxoids, was obtained.
Thus, by appropriate choice of reaction pathways usefully
functionalised AB-ring sub-structures (e.g. 20 and 33) associated with
both taxoids and ent-taxoids are accessible from the SAME readily
available chiron, viz the toluene-derived cis-1,2-dihydrocatechol 2.
7.
8.
Banwell, M. G.; Dupuche, J. R. Chem. Commun. 1996, 869.
Banwell, M. G.; Dupuche, J. R.; Gable, R. W. Aust. J. Chem.,
1996, 49, 639.
Acknowledgments. We thank Drs Larry Kwart and Gregg Whited
(Genencor International Inc.) for providing generous samples of
compound 2.
9.
For related examples of diastereoselective acetal formation see:
Oikawa, Y.; Nishi, T.; Yonemitsu, O. Tetrahedron Lett., 1983, 24,
4037.
10. Shiner, C. S.; Fisher, A. M.; Yacoby, F. Tetrahedron Lett., 1983,
24, 5687.
References and Notes
1.
Xiao, X.-Y.; Parandoosh, Z.; Nova, M. P. J. Org. Chem., 1997, 62,
11. Rylander, P. N. Aldrichimica Acta, 1979, 12, 53.
6029 and references cited therein.
12. Cristau, H.-J.; Ribeill, Y.; Chiche, L.; Plénat, F. J. Organomet.
Chem., 1988, 352, C47.
2.
(a) Holton, R. A.; Juo, R. R.; Kim, H. B.; Williams, A. D.;
Harusawa, S.; Lowenthal, R. E.; Yogai, S. J. Am. Chem. Soc.,
1988, 110, 6558; (b) Holton, R. A.; Kim, H.-B.; Somoza, C.;
Liang, F.; Biediger, R. J.; Boatman, P. D.; Shindo, M.; Smith, C.
C.; Kim, S.; Nadizadeh, H.; Suzuki, Y.; Tao, C.; Vu, P.; Tang, S.;
Zhang, P.; Murthi, K. K.; Gentile, L. N.; Liu, J. H. J. Am. Chem.
Soc., 1994, 116, 1599 and references cited there-in; (c) Nicolaou,
K. C.; Ueno, H.; Liu, J.-J.; Nantermet, P. G.; Yang, Z.; Renaud, J.;
Paulvannan, K.; Chadha, R. J. Am. Chem. Soc., 1995, 117, 653
and references cited there-in; (d) Danishefsky, S. J.; Masters, J. J.;
Young, W. B.; Link, J. T.; Snyder, L. B.; Magee, T. V.; Jung, D.
K.; Isaacs, R. C. A.; Bornmann, W. G.; Alaimo, C. A.; Coburn, C.
A.; Di Grandi, M. J.; J. Am. Chem. Soc., 1996, 118, 2843;
(e) Hara, R.; Furukawa, T.; Horiguchi, Y.; Kuwajima, I.; J. Am.
Chem. Soc., 1996, 118, 9186; (f) Wender, P. A.; Badham, N. F.;
Conway, S. P.; Floreancig, P. E.; Glass, T. E.; Houze, J. B.; Krauss,
N. E.; Lee, D.; Marquess, D. G.; McGrane, P. L.; Meng, W.;
Natchus, M. G.; Shuker, A. J.; Sutton, J. C.; Taylor, R. E. J. Am.
Chem. Soc., 1997, 119, 2757; (g) Mukaiyama, T.; Shiina, I.;
13. Ley, S. V.; Norman, J.; Griffith, W. P.; Marsden, S. P. Synthesis,
1994, 639.
14. A related cyclisation occurring within a similar framework has
been observed: Holton, R. A.; Williams, A. D. J. Org. Chem.,
1988, 53, 5981.
15. Foster, G.; Johnson, P. Chem. Abstr., 1970, 73, 131809a.
16. For related approaches to C oxygenation see references 2b,f.
13
17. Boyd, D. R.; Sharma, N. D.; Barr, S. A.; Dalton, H.; Chima, J.;
Whited, G.; Seemayer, R. J. Am. Chem. Soc., 1994, 116, 1147.
18. Ray, R.; Matteson, D. S. Tetrahedron Lett., 1980, 21, 449.
19. Crystal structure data have been deposited with the Cambridge
Crystallographic Data Centre (CCDC) and can be obtained by
directing enquiries to the following address: The Director, CCDC,
12 Union Road, Cambridge, CB2 1EZ, United Kingdom.
20. Swiss, K. A.; Hinkley, W.; Maryanoff, C. A.; Liotta, D. C.
Synthesis, 1992, 127.