Method for preparing cyclic ethers and thioethers including oxyg

Details Method for preparing cyclic ethers and thioethers including oxyg Method for preparing cyclic ethers and thioethers including oxyg

1978-03-13

1981-03-24

Trousof, Natalie

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

26034622, 549 53, C07D33378, C07D30793

Patent

active

042581990

ABSTRACT:
Unsaturated alcohols, thiols and thioesters are cyclized by a phenyl selenenyl halide; wherein the conformation flexibility of the unsaturated alcohol, thiol or thioester is selected such that the hydroxy group, thiol group or thioester group is capable of internal addition to at least one unsaturated bond in said alcohol, thiol or thioester; and wherein the ratio of the phenyl selenenyl halide to said unsaturated alcohol, thiol or thioester is 0.9-1.5 to 1. In a preferred embodiment, oxygen isomers and sulfur analogs of prostacyclin of the formula ##STR1## wherein X= ##STR2## Y=(E)- and (Z)- >C.dbd.CH--CH.sub.2 CH.sub.2 CH.sub.2 COOR; (E)- >CH--CH.dbd.CH--CH.sub.2 CH.sub.2 COOR; and

REFERENCES:
patent: 3881017 (1975-04-01), Vlattas
Corey, E. J. et al., "Synthesis of Vane's Prostaglandin X . . . ", J. Am. Chem. Society. (Communication) vol. 99 (Mar. 16, 1977), pp. 2006-2008.
Sharpless, K. B. et al., J. Org. Chem., vol. 39 (1974) pp. 429-430.
C&EN (Chemical & Engineering News) Dec. 20, 1976, pp. 17-19.
Bundy, G. L. et al., J. of the Am. Chem. Soc., vol. 94 (1972) p. 2124.
Royals, Earl E., Adv. Org. Chemistry (1963) p. 107.
Reid, E. Emmet, Org. Chem. of Bivalent Sulfur (1960) pp. 11, 12.
Brown, Herbert C., Organometallics in Chemical Synthesis, vol. 1 1970/1971, pp. 7-22.

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