7502
REFERENCES AND NOTES.
1.
2.
3.
S. L.; Fang, Q. J. Org.
Johnson, F.; Subramanian, R. J. Org.
Reinheimer, J. D.; Taylor, R. C.; Rohrbaugh, P. E. J. Am.
E. W.; Pruitt, K. M. ibid 385.
1989.54, 2793.
5040.
835.
J. F.;
1951. 2340.
C. W. L. J.
Beckwith. A. L.; Miller, D.;
G. D. ibid, 1952 3552. Idoux. J. P.; Madenwald, M. L.; Garcia, B.
S.; Chu, D.-L.; Gupton, J. T. J. Org.
1876.
4.
Chu. D. T. W.; Prabhavathi, B. F.; Akiyo, K. C.; Pihuleac, E.; Nordeen, C. W.; Maleczka, R. E.;
A. G. J. Med. Chem.
1558. Miyamoto. T.; Matsumoto, J.;
K.; Egawa, H.;
K.; Minamida, A.; Nishimura, Y.;
H.; Kataoka, M.;
M.;
T.; Nakano.
J. ibid
1645. Sanchez, J. P.; Domagala, J. M.;
S. E.; Heifetz, C. L.; Hutt, M. J.;
Nichols, J. B.; Trehan. A. K. ibid
983.
5.
6.
Streitweiser, A.; Mares. F. J. Am.
644. Streitweiser. A.; P. J.;
Niemeyer, H. M. ibid
7936. Bridges, A. J.; Patt, W. C.; Stickney, T. M. J. Org. Chem
1990.55. 773.
Semmelhack, M. F.; Bisaha, J.; Czarny, M. J. Am. Chem
1979,101, 768. Meyers, A.
B. E. Tetrahedron
1978,223. Sanchez, J. P.; Bridges, A. J.; Busch, R.; Domagala,
J. M.; Gogliotti, R. D.;
S. E.; Heifetz, C. L.; Joannides, E. T.; Sesnie, J. C.; Shapiro, M. A.;
Szotek, D. L. J. Med. Chem 1992.35, 361. Domagala, J. M.; Bridges, A. J.; Culbertson, T. P.;
Gambino, L.;
Szotek, D. L.; Wemple. J. ibid
Bridges, A. J.; Lee, A.; Maduakor. E. C.; Schwartz, C.
S. E.; Karrick, G.; Portere, K.; Sanchez, J. P.; Sesnie, J. C.;
F. G.;
10 mmol)
DMF
1142.
7.
see preceding paper “this journal.
8. A sample experimental for Entry 3 is described: n-Butyllithium (2.3 M in hexanes, 4.35
was added
over 5 min to a solution of diisopropylamine (1.113 g, 11 mmol) in THF (20
stirred under
at
After 10
(1.643 g, 10.0 mmol) was added
11 mmol) was added over 5 min. After a further 10 min at
the reaction mixture was cooled to
and
over 5 min. After 1 h at
(0.80
the reaction mixture
The cold
washed
The
was quenched by the rapid addition of acetic acid (2
solution was quickly extracted with ether (3 x 25
followed quickly by
and the combined organic extracts
saturated brine (25 and dried
removed under reduced pressure to give crude
(1.85 g, 18% by weight solvent, 80%) as a light yellow oil:
(50
with dilute
(0.2 M. 25
water (25
solvent was
NMR (CDC13) 10.43
sl br s), 7.69
sl br dt, J = 5.2, 8.0 Hz), 7.62
br d, J = 7.6 Hz),
7.42
br dd. J = 8.4, 10.2 Hz).
Methyl thioglycollate (0.72
8
was added over 10 min to a
suspension of
hexanewashed
(60% oil suspension, 0.50 g, 12.5 mmol) in DMSO (10
stirred under
on a
water bath. When gas evolution died down the bath was removed and the light yellow solution was
for 15 min. Crude
mmol) in DMSO (2
(1.85 g, 18% by weight solvent, 8
was added rapidly, and an exotherm, gas evolution and considerable darkening of
the reaction mixture were observed. After 3 min the mixture was poured onto rapidly stirred ice-water
(100 and the precipitate was collected by suction filtration, rinsed with water (2 x 25 and air
dried to give methyl
pale beige powder:
7.5, 0.7 Hz), 7.54
(1.17 g, 56%) as
a
NMR (CDC13) 8.27
sl br dd, J
sl br s). 8.06
s).
d, J = 8.2 Hz), 7.73
dq. J =
Hz), 3.98
9.
10. Heck, R. F. “Palladium Reagents in
Stille, J. K. Angew. Chem., Ed.
Mills, R. J.; Taylor, N. J.;
V. J. Org. Chem..
4372.
Syntheses,” Academic Press, London, 1985. pp. 299-306.
508.
(Received in USA 14 May 1992; accepted 2 September 1992)