various cis-1,2-dihydrocatechols is the preferred reaction pathway at
7 For an excellent review on the production and general synthetic
utility of these types of compounds see T. Hudlicky, D. Gonzalez
and D. T. Gibson, Aldrichimica Acta, 1999, 32, 35.
8 (a) M. Banwell and M. McLeod, Chem. Commun., 1998, 1851; (b)
M. G. Banwell, P. Darmos, M. D. McLeod and D. C. R. Hockless,
Synlett, 1998, 897.
9 D. R. Boyd, N. D. Sharma, S. A. Barr, H. Dalton, J. Chima,
G. Whited and R. Seemayer, J. Am. Chem. Soc., 1994, 116, 1147.
10 J. R. Gillard and D. J. Burnell, J. Chem. Soc., Chem. Commun., 1989,
1439.
11 (a) For useful discussions on factors controlling the facial
selectivities observed in the Diels–Alder reactions of dissymmetric
dienes see R. Uma and G. Mehta, Acc. Chem. Res., 2000, 33, 278;
(b) J. M. Coxon, R. D. J. Froese, B. Ganguly, A. P. Marchand and
K. Morokuma, Synlett, 1999, 1681.
1
¶
9 kbar.
Crystal data for 12: C H O , M = 308.418, T = 200(1) K, ortho-
1
8
28
4
rhombic, space group P2 2 2 , Z = 4, a = 6.08980(10), b = 11.0181(2),
c = 25.4436(5) Å, V = 1707.22(5) Å , D = 1.200 Mg m , 1770 unique
1
1 1
3
Ϫ3
x
data (2Θmax = 50.06Њ), 1268 with I > 2σ(I); R = 0.0297, Rw = 0.0334,
S = 1.0303.
Images were measured on a Nonius Kappa CCD diffractometer
(
MoKα, graphite monochromator, λ = 0.71073 Å) and data extracted
19
using the DENZO package. Structure solution was by direct methods
20
(
SIR97) and refinement was by full matrix least-squares on F using
2
1
the CRYSTALS program package. Atomic coordinates, bond lengths
and angles, and displacement parameters have been deposited at the
Cambridge Crystallographic Data Centre (CCDC reference number
1
92411. See http://www.rsc.org/suppdata/p1/b2/b208778b/ for crystal-
lographic files in .cif or other electronic format.).
12 (a) D. H. R. Barton and S. W. McCombie, J. Chem. Soc., Perkin
Trans. 1, 1975, 1574; (b) For reviews see W. Hartwig, Tetrahedron,
1983, 39, 2609 as well as D. Crichand L. Quintero, Chem. Rev., 1989,
89, 1413.
1
For reviews see (a) L. A. Paquette, Top. Curr. Chem., 1979, 79, 41;
b) B. M. Trost, Chem. Soc. Rev., 1982, 11, 141; (c) M. Demuth
(
and K. Schaffner, Angew. Chem., Int. Ed. Engl., 1982, 21, 829; (d )
G. Metha and A. Srikrishna, Chem. Rev., 1997, 97, 671; (e) V. Singh
and B. Thomas, Tetrahedron, 1998, 54, 3647.
(a) T. C. Feline, G. Mellows, R. B. Jones and L. Phillips, J. Chem.
Soc., Chem. Commun., 1974, 63; (b) S. Nozoe, J. Furukawa,
U. Sankawa and S. Shibata, Tetrahedron Lett., 1976, 195.
13 M. G. Banwell, V. S. Bridges, J. R. Dupuche, S. L. Richards and
J. M. Walter, J. Org. Chem., 1994, 59, 6338.
14 E. J. Corey, J.-L. Gras and P. Ulrich, Tetrahedron Lett., 1976, 809.
MEM-protection was employed at this point in order to prevent
decomposition of the product of the subsequent photo-iso-
merisation step.
2
3
4
5
6
P. F. Schuda, J. L. Phillips and T. M. Morgan, J. Org. Chem., 1986,
15 R. A. Batey and W. B. Motherwell, Tetrahedron Lett., 1991, 32, 6649
5
1, 2742 and references cited therein.
and references cited therein.
G. Mehta and D. S. Reddy, J. Chem. Soc., Perkin Trans. 1, 2001, 1153
and references cited therein.
16 V. Singh and M. Porinchu, Tetrahedron, 1996, 52, 7087.
17 H. Monti, G. Léandri, M. Klos-Ringuet and C. Corriol, Synth.
Commun., 1983, 13, 1021.
18 D. J. Watkin, C. K. Prout and L. J. Pearce, CAMERON, Chemical
Crystallography Laboratory, Oxford, UK, 1996.
19 DENZO-SMN. Z. Otwinowski and W. Minor, Processing of
X-ray diffraction data collected in oscillation mode, Methods in
Enzymology, Volume 276: Macromolecular Crystallography, Part
A, eds. C. W. Carter, Jr., and R. M. Sweets, Academic Press, 1997,
pp. 307–326.
20 A. Altomare, M. C. Burla, M. Camalli, G. L. Cascarano, C. Giacov-
azzo, A. Guagliardi, A. G. G. Moliterni and R. Spagna, J. Appl.
Crystallogr., 1999, 32, 115.
F. Geng, J. Liu and L. A. Paquette, Org. Lett., 2002, 4, 71 and
references cited therein.
(a) D. H. Hua, S. Venkataraman, R. A. Ostrander, G.-Z. Sinai,
P. J. McCann, M. J. Coulter and M. R. Xu, J. Org. Chem., 1988, 53,
5
07; (b) J. Castro, H. Sörensen, A. Riera, C. Morin, A. Moyano,
N. A. Pericãs and A. E. Greene, J. Am. Chem. Soc., 1990, 112, 9388;
c) T. Inoue, K. Hosomi, M. Araki, K. Nishide and M. Node, Tetra-
(
hedron: Asymmetry, 1995, 6, 31; (d ) T. Anger, O. Graalmann,
H. Schroder, R. Gerke, U. Kaiser, L. Fitjer and M. Noltemeyer,
Tetrahedron, 1998, 54, 10713; (e) J. Leonard, L. Bennett and
A. Mahmood, Tetrahedron Lett., 1999, 40, 3965; ( f ) V. Singh,
P. Vedantham and P. K. Sahu, Tetrahedron Lett., 2002, 43, 519. For
discussions of syntheses of hirsutene reported prior to 1997–1998
see references 1(d) and 1(e).
21 D. J. Watkin, C. K. Prout, J. R. Carruthers, P. W. Betteridge and
R. I. Cooper, CRYSTALS Issue 11, Chemical Crystallography
Laboratory, Oxford, UK, 2001.
J. Chem. Soc., Perkin Trans. 1, 2002, 2439–2441
2441