3
778
D. A. Lanfranchi et al.
PAPER
T. Org. Lett. 2002, 4, 4483. (n) Terpentecine: Ling, T.;
2
0
were dried under high vacuum at r.t.; [a] –140 (c = 1.0, CH Cl )
D
2
2
2
20
{
Lit. [a] –140 (c = 1.0 in CH Cl )}. The spectroscopic and phys-
Rivas, F.; Theodorakis, E. A. Tetrahedron Lett. 2002, 43,
9019. (o) Almstead, J.-I. K.; Demuth, T. P. Jr.; Ledoussal, B.
Tetrahedron: Asymmetry 1998, 9, 3179. (p) (+)-Aureol:
Suzuki, A.; Nakatani, M.; Nakamura, M.; Kawaguchi, K.;
Inoue, M.; Katoh, T. Synlett 2003, 329. (q) (–)- and (+)-
Cacospongionolides: Cheung, A. K.; Murelli, R.; Snapper,
M. L. J. Org. Chem. 2004, 69, 5712. (r) (–)-Methyl
barbascoate: Hagiwara, H.; Hamano, K.; Nozawa, M.;
Hoshi, T.; Suzuki, T.; Kido, F. J. Org. Chem. 2005, 70,
2250. (s) (+)-Aureol: Sakurai, J.; Oguchi, T.; Watanabe, K.;
Abe, H.; Kanno, S.-I.; Ishikawa, M.; Katoh, T. Chem. Eur. J.
2008, 14, 829. (t) Salvinorin A: Nozawa, M.; Suka, Y.;
Hoshi, T.; Suzuki, T.; Hagiwara, H. Org. Lett. 2008, 10,
1365.
D
2
2
2
ical data were identical to those reported in the literature.
(
–)-(R)-5,5-(Ethylenedioxy)-1,4a-dimethyl-4,4a,5,6,7,8-hexahy-
dro-2(3H)-naphthalenone (9)
Raney Ni (11.35 g wet, 50% in H O) was rinsed successively with
2
distilled H O (2 × 50 mL) and MeOH (3 × 50 mL) and acetone (3 ×
2
5
0 mL). The activated Raney Ni was added to acetone (60 mL) un-
der argon. The mixture was refluxed for 30 min. A solution of 8
600 mg, 1.743 mmol) dissolved in acetone (5 mL) was then added
(
to the warm acetone solution. The refluxing was continued for 6 h.
After cooling down, the catalyst was removed by filtration on
Celite. The filter cake was rinsed with acetone (3 × 40 mL). Ace-
tone was removed under reduced pressure leaving a yellow oil,
which was purified by flash chromatography [silica gel, hexanes–
(2) Hagiwara, H.; Uda, H. J. Org. Chem. 1988, 53, 2308.
(3) (a) Tamai, Y.; Mizutani, Y.; Hagiwara, H.; Uda, H.; Harada,
N. J. Chem. Res., Miniprint 1985, 148. (b) Tamai, Y.;
Mizutani, Y.; Hagiwara, H.; Uda, H.; Harada, N. J. Chem.
Res., Miniprint 1985, 1746.
(4) Corey, E. J.; Virgil, S. C. J. Am. Chem. Soc. 1990, 112, 6429.
5) Agami, C.; Kadouri-Pouhot, C.; Le Guen, V. Tetrahedron:
Asymmetry 1993, 4, 641.
EtOAc (3:1); R = 0.3]; yield: 371 mg (90%); very pale yellow oil;
f
20
15
20
[
a]D –110 (c = 0.5, MeOH) {Lit.
[a]D –109 (c = 0.53,
MeOH)}.
The spectroscopic and physical data were identical to those reported
in the literature.14,15
(
(
6) (a) Uma, R.; Swaminathan, S.; Rajagopalan, K. Tetrahedron
Lett. 1984, 25, 5825. (b) Uma, R.; Swaminathan, S.;
Rajagopalan, K. Tetrahedron 1986, 42, 2757. (c) This work
was not mentioned in Hagiwara–Uda’s papers.
Acknowledgment
This work was supported by the Collectivité Territoriale Corse,
CNRS and ECPM of Strasbourg.
(
7) Heathcock, C. H.; Mahaim, C.; Schlecht, M. F.; Utawanit, T.
J. Org. Chem. 1984, 49, 3264.
References
(
8) (a) Swaminathan, S.; Newman, M. S. Tetrahedron 1958, 2,
8
8. (b) Born, H.; Pappo, R.; Szmuszkovicz, J. J. Chem. Soc.
(
1) (a) (+)-Dysideapalaunic acid: Hagiwara, H.; Uda, H.
J. Chem. Soc., Perkin Trans. 1 1991, 1803. (b) trans-
Clerodane: Hagiwara, H.; Inome, K.; Uda, H. J. Chem. Soc.,
Perkin Trans. 1 1995, 757. (c) (–)-Illimaquinone: Brunner,
S. D.; Radeke, H. S.; Tallarico, J. A.; Snapper, M. L. J. Org.
Chem. 1995, 60, 1114. (d) See also: Poigny, S.; Guyot, M.;
Samadi, M. J. Org. Chem. 1998, 63, 5890.
1953, 1779. (c) Meek, E. G.; Turnbull, J. H.; Wilson, W. J.
Chem. Soc. 1953, 811.
(
9) The recrystallized diketone 1 obtained by Snapper et al. had
a better ee (93% vs 82%) compared to enantiomerically pure
1
q
material.
10) (a) Gutzwiller, J.; Buchschacher, P.; Fürst, A. Synthesis
977, 167. (b) Buchschacher, P.; Fürst, A.; Gutzwiller, J.
Org. Synth. Coll. Vol. VII; Wiley: New York, 1990, 368–
72.
(
1
(
e) Illimaquinone analogues: Radeke, H. S.; Digits, C. A.;
Brunner, S. D.; Snapper, M. L. J. Org. Chem. 1997, 62,
823. (f) (+)-Arenarol: Kawano, H.; Itoh, M.; Katoh, T.;
3
2
(
(
11) Baudoin, G.; Pietrasanta, Y. Tetrahedron 1973, 29, 4225.
12) (a) Kirk, D. N.; Petrow, V. J. Chem. Soc. 1962, 1091.
Terashima, S. Tetrahedron Lett. 1997, 38, 7769. (g) (–)-
Dysidiolide: Corey, E. J.; Roberts, B. E. J. Am. Chem. Soc.
(
3
b) Smith, A. B. III.; Mewshaw, R. J. Org. Chem. 1984, 49,
685.
1
997, 119, 12425. (h) Akaterpin: Kawai, N.; Takao, K.-I.;
Kobayashi, S. Tetrahedron Lett. 1999, 40, 4193. (i) Avarol:
Ling, T.; Xiang, A. X.; Theodorakis, E. A. Angew. Chem.
Int. Ed. 1999, 38, 3089. (j) Clerocidine: Markó, I. E.;
Wiaux, M.; Warriner, S. M.; Giles, P. R.; Eustace, P.; Dean,
D.; Bailey, M. Tetrahedron Lett. 1999, 40, 5629.
(
(
(
13) (a) Spero, G. B.; McIntosh, A. V.; Levin, R. H. J. Am. Chem.
Soc. 1948, 70, 1907. (b) Rosenkranz, G.; Kaufmann, S.;
Romo, J. J. Am. Chem. Soc. 1949, 71, 3689.
14) Markò, I. E.; Ates, A.; Gautier, A.; Leroy, B.; Plancher,
J.-M.; Quesnel, Y.; Vanherck, J.-C. Angew. Chem. Ed. Int.
(
k) Nakijiquinones: Stahl, P.; Waldmann, H. Angew. Chem.
1999, 38, 3207.
Int. Ed. 1999, 38, 3710. (l) Sesquiterpenes: Ling, T.;
Poupon, E.; Rueden, E. J.; Kim, S. H.; Theodorakis, E. A. J.
Am. Chem. Soc. 2002, 124, 12261. (m) (+)-Stachyfin:
Nakatani, M.; Nakamura, M.; Suzuki, A.; Inoue, M.; Katoh,
15) Tadashi, K.; Mari, N.; Shoji, S.; Ruriko, S.; Akihiro, I.;
Osamu, O.; Masahiko, N.; Terashima, S. Org. Lett. 2001, 3,
2701.
Synthesis 2008, No. 23, 3775–3778 © Thieme Stuttgart · New York