ABSTRACT
The synthesis of prostaglandin analogs incorporating the (2-hydroxycyclooctylidene)methyl moiety in place of the natural C13-C20 sidechain has been accomplished via copper-assisted conjugate addition of the (cyclooctylidene)methyllithium 5 to the cyclopentenone intermediates 7 and 10.
Subject(s)
Prostaglandins/chemical synthesis , Chemical Phenomena , Chemistry , Cycloparaffins/chemical synthesisABSTRACT
The synthesis of prostaglandin analogs incorporating the 3-hydroxycyclohexenyl moiety in place of the natural C13-C20 side-chain has been accomplished via copper-assisted conjugate addition of the cycloalkenyllithium 2 to the cyclopentenous intermediates 4, 7 and 10.
Subject(s)
Prostaglandins/chemical synthesis , Animals , Cyclohexanols/chemical synthesis , Cyclopentanes , Guinea Pigs , Ileum/drug effects , In Vitro Techniques , Muscle Contraction/drug effects , Prostaglandins/pharmacologyABSTRACT
Penicillium adametzi and seven other species convert nalidixic acid, 1,4-dihydro-1-ethyl-7-methyl-4-oxo-1,8-naphthyridine-3-carboxylic acid, to 1,4-dihydro-1-ethyl-7-hydroxymethyl-4-oxo-1,8-naphthyridine-3-carboxylic acid. Forty-seven other species from six orders of fungi seem to achieve the same conversion as judged by chromatographic and spectral evidence. Under special conditions, P. adametzi also produces a second metabolite which was identified as the corresponding 7-carboxylic acid. The metabolic attack on the ring substituent is identical with the pathway previously established with humans. No evidence was obtained for metabolic attack on the naphthyridine nucleus itself.