Periplanone-B analogues as well as cockroach attractant

Details Periplanone-B analogues as well as cockroach attractant Periplanone-B analogues as well as cockroach attractant

1990-10-16

1992-06-30

Rotman, Alan L.

Drug, bio-affecting and body treating compositions

Baits, attractants, or lures

549332, 549546, 549215, A01N 2500, C07D30318

Patent

active

051261286

ABSTRACT:
Periplanone-B analogue of (4E, 8R, 9R, 10R)-8,9-epoxy-5-methyl-10,10-methylene-oxy-4-cyclodecen-1-one, suitable as cockroach attractant can be prepared by reacting 6-methyl-2,6-cyclodecadien-1-one with a silylating reagent under the presence of a basic catalyst to form a silyldienol ether, reacting the resultant ether with an organic peracid to obtain (2Z, 6E)-10-hydroxy-6-methyl-2,6-cyclodecadien-1-one, reacting the resultant product with a peroxide under the presence of a basic catalyst after protecting hydroxy groups thereof with protection groups to obtain an epoxide, reacting the epoxide with chloromethyl lithium or dimethyl sulfonium methylide thereby introducing a spiroepoxy group and then removing the protection groups, to obtain (1S, 4E, 8R, 9R, 10S)-8,9-epoxy-5-methyl-10,10-methyleneoxy-4-cyclodecen-1-ol and, further, oxidizing the resultant product with a chromic acid type or dimethyl sulfoxide type oxidizing agents.

REFERENCES:
patent: 4639532 (1987-01-01), Schreiber
patent: 4755626 (1988-07-01), Mori et al.
patent: 4911907 (1990-03-01), Shimamura et al.
patent: 4980485 (1990-12-01), Mori et al.
Persoons et al., Tetrahedron Letters, No. 24, pp. 2055-2058 (1976).
Greigger et al., Jounal of the American Chemical Society, 101:9, pp. 2493-2494 (1979).
Still, Journal of the American Chemical Society, 101:9, pp. 2495-2498 (1979).
Schreiber et al., J. Am. Chem. Soc., 106, pp. 4038-4039 (1984).
Hauptmann et al., Tetrahedron Letters, vol. 27, No. 12, pp. 1315-1318 (1986).
Kitahara et al., Tetrahedron Letters, vol. 27, No. 12, pp. 1343-1346 (1986).
Takahashi et al., J. Org. Chem., 51, pp. 3393-3394 (1986).
De Clercq et al., Tetrahedron Letters, vol. 29, No. 49, pp. 6501-6504 (1988).
Persoons et al., J. Chem. Ecol., 5, pp. 221-237 (1979).
Hauptmann et al., Tetrahedron Letters, vol. 27, No. 51, pp. 6189-6192 (1986).
Bowers et al., Nature, vol. 232, pp. 259-261 (1971).
Tahara et al., Agr. Biol. Chem., 39 (7), pp. 1517-1518 (1975).
Nishino et al., Appl. Ent. Zool., 12 (3), pp. 287-290 (1977).

Affiliated with

Also associated with

Rating

Periplanone-B analogues as well as cockroach attractant does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Periplanone-B analogues as well as cockroach attractant, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Periplanone-B analogues as well as cockroach attractant will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-1862446