13C NMR spectra of biologically active compounds. II. 11-Deoxy-16- and 17-aryloxyprostaglandins

Толстиков, Г. А.; Халилов, Л. М.; Panasenko, A. A.; Данилова, М. Н.; Miftakov, M. S.

doi:10.1007/bf00579054

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(1 citation statement)

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“…For papers that report original research, you should use the titles "Materials and Methods", "Results", "Discussion" and "Conclusions" (optional). In a sequence, the diacids [4] were transformed in the anhydrides [5] which, by reaction of the lithium salt of dimethyl methanephosphonate (DMMPh) (generated in situ from DMMPh and n-BuLi in and. THF at low temperature (below −70 °C)), gave the β-ketophosphonates 2 (R = OH).…”

Section: Introductionmentioning

confidence: 99%

Key Intermediates for introducing a bulky bicyclo[3.3.0]heptane skeleton in the w-side chain to reduce the enzyme inactivation of prostaglandins

Tănase

Drăghici²,

Căproiu³

2020

Proceedings of the 24th International Electronic Conference on Synthetic Organic Chemistry

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In vivo, the prostaglandins (PGs) are inactivated by enzyme oxidation of the 15-α-OH group to 15-keto group. 15-, 16-Substituents, 16-Aryloxy and others diminished this inactivation [1]. We planed to diminish inactivation by introducing bulky bicyclo[3.3.0]octane or bicyclo[3.3.0]oct-6-ene substituents linked to the C-15 carbon atom, but also to introduce this fragment found in nature and in compounds with anticancer activity. ω-Side chain of PGs are introduced by an E-HEW-stereoselective olefination of an aldehyde with a β-ketophosphonate (Corey procedure). The β-ketophosphonates were synthesized from bicyclo[3.3.0]oct(a)ene acids by a two or three step sequence in good yields and used for obtaining a new PG.

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Section: Introductionmentioning

confidence: 99%