Conversion of iridoids to prostaglandins

Details Conversion of iridoids to prostaglandins Conversion of iridoids to prostaglandins

1981-09-25

1983-10-18

Fan, Jane T.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

536 41, 536 181, 549298, 549299, C07D30793

Patent

active

044107102

ABSTRACT:
Naturally occurring iridoids provide the starting material for a unique synthesis sequence to produce prostaglandin intermediates. The iridoid lactone is hydrogenated, converted to an acetal, and rings opened to introduce the carbonyl octenyl side chain in six steps. The intermediate can be converted to prostaglandin as previously demonstrated.

REFERENCES:
Berkowitz et al., J. Org. Chem., 1982, 47, 824-829.
Berkowitz et al., (I) Tetrahedron Letters, No. 19, pp. 1641-1644, 1979.
Naruto et al., Tetrahedron Letters, No. 3, pp. 251-254, 1979.
Berkowitz et al., (II) Tetrahedron Letters, vol. 22, pp. 1075-1076, 1981.
Fieser & Fieser, Reagents for Organic Synthesis, vol. 4, p. 151.

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