Method of manufacturing optically-active periplanone-b

Details Method of manufacturing optically-active periplanone-b Method of manufacturing optically-active periplanone-b

1989-09-26

1990-12-25

Hollrah, Glennon H.

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

549529, 549512, 549519, 549522, 549546, 560152, 558 52, 568 42, 568 37, 568497, 568601, 568 37, 568821, C07D30318, C07D30112

Patent

active

049804855

ABSTRACT:
Optically active periplanone-B is manufactured through oxidizing (1RS, 4S, 5E)-isopropyl-7-methylene-5-cyclodecene-1-ol. The oxidized product is regioselectively enolized and then sulfenylated. The sulfenylated product is oxidized and then subjected to decomposition of the sulfoxide. The decomposed product is epoxidated, and the epoxidated product is converted into an enolate which is then oxidized. The oxidized product is oxidized and then regio- and stereoselectively epoxidated to obtain optically active periplanone-B.

REFERENCES:
T. Kitahara et al., (I), Tetrahedron Letters, "Total Synthesis of (-)-Periplanone B . . . ", 27 (12) pp. 1343-1346, (1986).
T. Kitahara et al., (II), Tetrahedron "Total Synthesis of (-)-Periplanone B . . . ", 43 (12), pp. 2689-2699, (1987).
B. M. Troast, et al., J. Am. Chem. Soc., "New synthetic reactions, Sulfenylations and Dehydrosulfenylations . . . ", 98, pp. 4887-4902, (1976).
E. Vedejs, et al., J. Org. Chem., "Transitional-Metal Peroxide Reactions, Synthesis of .alpha.-Hydroxycarbonyl Compds. . . ", 43, pp. 188-196, (1978).
E. Vedejs, et al., J. Am. Chem. Soc., "A Method for Direct Hydroxylation of Enolates, Transition Metal Peroxide Reactions", 96, pp. 5944-5946, (1974).
S. P. Tanis et al., J. Am. Chem. Soc., "Stereospecitic Total Synthesis of (.+-.)-War-Gurganol, and related compounds", 101, 4398-4000, (1979).
F. A. Carey, and R. J. Sundberg, Adv. Organic Chemistry, 2nd Ed., Chapter 10, pp. 481-490, .COPYRGT.Plenum Press, New York, (1983).
C. J. Persoons, et al., Tetrahedron Letters, "Sex Pheromones of the American cockroach, Periplaneta Americana . . .", No. 24, pp. 2055-2058, (1976).
Fukuda, E. K., et al., J. Am. Chem. Soc., "Sex Pheromones of the American Cockroach:Absolute Configuration of Perplanone B", 101, pp. 2495-2499, (1979).
S. L. Schreiber, et al., J. Am. Chem. Soc., "Cyclobutene Bridgehead Olefin route to the American Cockroach sex pheromone. . .", 106, pp.4038-4039, (1984).
W. C. Still, J. Am. Chem. Soc., "(.+-.)-Periplanone-B, Total Synthesis and Structure of sex excitant pheromone of the . . . ", 101, pp. 2493-2495, (1979).

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