Prostaglandin analogs, synthesis

An analogous study concerned with the synthesis of prostaglandin analogs was also highly diastereoselective. The initial anionic adducts were quenched with various aldehydes, however, the diastereoselectivity at the carbinol stereocenter was not reported21. 

Collins, P. W. Synthesis of Therapeutically Useful Prostaglandin and Prostaglandin Analogs, Chem. Rev. 1993, 93, 1533. 

E xides and oxetanes react readily with lithiodithiane to give derivatives of 3- or y-hydroxy aldehydes or ketones. The method has been used for the multistep synthesis of an inomycin fragment, thietane prostaglandin analogs, branched-chain nucleoside sugars, the southern hexahydrobenzctfu-ran unit avermectin, the anti-Gram-positive bacterial elaiphylin andsyn-l,3-polyols. ... 

Lieb, F., 2-OxoaIkanephosphonic acid diaUcylesters useful in the synthesis of prostaglandin analogs, Bayer A.-G., German Patent Appl. DE 2711009, 1978 Chem. Abstr, 89, 215553, 1978. 

Numerous synthetic applications of the inteimolecular Pauson-Khand reaction have been reported. Pauson has reported a number of very direct tqrplications of cycloadditions of ethylene in the synthesis of prostanoids and jasmone analogs (e.g. equations 15 and 16). - This is a reliable entry to 2-sub-stituted cyclopentenones. The suitability of cyclopentene and dihydrofuran as substrates has permitted the extension of this work to the preparation of still further varieties of prostaglandin analogs (e.g. equations 27 and 51). Simple 4,5-disubstituted 2-cyclopentenones are not as directly accessible, but may be prepared from the cycloaddition products of norbomadiene (equation 45). A sequence of conjugate addition followed by retro-Diels-Alder reaction affords the product (Scheme 5). Dihydrofuran cycloadditions have been used by Billington in the syntheses of the antibiotic methylenomycin B (Scheme 6), as well as cyclomethylenomycin A (synthetic precursor to the antibiotic methylenomycin A), cyclosarko-mycin (precursor to the antitumor agent sarkomycin) ° and the iridoid Jq>anese hop ether. ... 

Since several excellent recent reviews of prostaglandin chemistry are available (14.15.16), we will limit the chemical discussion to the development at Lederle and elsewhere of the synthesis of prostaglandin analogs by the convergent conjugate-addition approach and by the derivatization of I-PGA2, available 0-8412-0536-l/80/47-118-301 16.40/0 1980 American Chemical Society... 

Synthesis and biological activity of prostaglandin analogs containing het-eroatoms in the cyclopentane ring 05CCXi 419. 

L-selectride/cleavage with HF to that described earlier for Chen and Janda s synthesis gave 378. In addition to the synthesis of those prostaglandins described herein, both Chen and Janda and the Ellman group used their chemistry in the solid-phase synthesis of libraries of prostaglandin analogs. 

The necessity for producing large amounts of synthetic prostaglandins and analogs provided the impetus for a number of improvements in the bicyclo[2.2.1]heptene approach. Especially important was the development of an enantioselective modification for the synthesis of chiral prostanoids without resolution (1975) and the invention of a chiral catalyst for the stereocontrolled conversion of 15-keto prostanoids to either 15(5)- or 15(7 )- alcohols. 

Synthesis of Several Analogs of the Prostaglandin Endoperoxide PGH2... 

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