Synthesis of (R)-6,7-dihydro-5-HETE lactone and (S)-6,7-dihydro-5-HETE lactone by using novel yeast reduction as a key reaction

Yamauchi, Satoshi; Takeda, Kenji; Ganaha, Makoto; Kinoshita, Yoshiro

doi:10.1039/b206843p

Cited by 12 publications

(1 citation statement)

References 9 publications

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“…(R)- and (S)-6,7-dhydro-5-HETE lactones 89 were synthesized by linking a key chiral aldehyde intermediate 85 with the yield generated in situ from the triphenylphosphonium bromide 86 in a cis -selective Wittig reaction with the generation of the triene 87a in a 68% yield. The deprotection of the trityl group (71%), followed by the oxidation to 1-carboxylic acid (73%), and the final acid cleavage of the MOM ether, gave directly the (R)-6,7-dihydro-5-HETE lactone 89 at a 92% yield ( Scheme 18 ) [ 57 ]. (S)-isomer 89 was obtained by the same sequence of reactions starting from the enantiomer 85 .…”

Section: Lactones In the Synthesis Of Prostaglandins And Prostaglamentioning

confidence: 99%

Lactones in the Synthesis of Prostaglandins and Prostaglandin Analogs

Tănase

Pintilie

Tănase

2021

IJMS

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In the total stereo-controlled synthesis of natural prostaglandins (PGs) and their structural analogs, a vast class of compounds and drugs, known as the lactones, are encountered in a few key steps to build the final molecule, as: δ-lactones, γ-lactones, and 1,9-, 1,11-, and 1,15-macrolactones. After the synthesis of 1,9-PGF2α and 1,15-PGF2α lactones, many 1,15-lactones of E2, E3, F2, F3, A2, and A3 were found in the marine mollusc Tethys fimbria and the quest for understanding their biological role stimulated the research on their synthesis. Then 1,9-, 1,11-, and 1,15-PG lactones of the drugs were synthesized as an alternative to the corresponding esters, and the first part of the paper describes the methods used for their synthesis. The efficient Corey procedure for the synthesis of prostaglandins uses the key δ-lactone and γ-lactone intermediates with three or four stereocenters on the cyclopentane fragment to link the PG side chains. The paper describes the most used procedures for the synthesis of the milestone δ-Corey-lactones and γ-Corey-lactones, their improvements, and some new promising methods, such as interesting, new stereo-controlled and catalyzed enantioselective reactions, and methods based on the chemical/enzymatic resolution of the compounds in different steps of the sequences. The many uses of δ-lactones not only for the synthesis of γ-lactones, but also for obtaining 9β-halogen-PGs and halogen-substituted cyclopentane intermediates, as synthons for new 9β-PG analogs and future applications, are also discussed.

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Section: Lactones In the Synthesis Of Prostaglandins And Prostaglamentioning

confidence: 99%