Synthesis of bicyclic and tricyclic 7-oxa prostaglandin endopero

Details Synthesis of bicyclic and tricyclic 7-oxa prostaglandin endopero Synthesis of bicyclic and tricyclic 7-oxa prostaglandin endopero

1983-03-03

1985-08-13

Gerstl, Robert

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

Organic compounds

Carboxylic acid esters

560120, 562499, 562502, C07C17700

Patent

active

045351791

ABSTRACT:
Bicyclic oxa prostaglandin endoperoxide analogs, and tricyclic oxa prostaglandin analogs are prepared by reacting norbornadiene palladium dichloride with tertiary butyl-6-hydroxyhexanoate in an oxypalladation reaction to provide an oxypalladium intermediate which can subsequently be elaborated into bicyclic and/or tricyclic 7-oxa prostaglandin endoperoxides. If the intermediate is carbonylated in the presence of an organic amine, preferably diisopropylethylamine, the compound is bicyclic; if the amine is eliminated, the compound is tricyclic. The analogs are novel compounds.

REFERENCES:
patent: 4113755 (1978-09-01), Larock
patent: 4351949 (1982-09-01), Larock
Larock et al., Tet. Letters, 23, 1071, 715, (1982).
March, Advanced Organic Chemistry, 2nd ED., pp. 284-302, (1977).

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