Diastereodivergent Synthesis of A-Ring Lactones Derived from Cholesterol and Diosgenin: A Convenient Solution for an Old Problem - NMR and X-ray Characterization

被引：1

作者：

Garcia-Santos, William H. ^{[1
]}

Valente-Valdovinos, Paola ^{[1
]}

Cortina-Mendoza, Alvaro J. ^{[1
]}

Flores-Alamo, Marcos ^{[1
]}

Iglesias-Arteaga, Martin A. ^{[1
]}

机构：

[1] Univ Nacl Autonoma Mexico, Fac Quim, Ciudad Univ, Mexico City 04510, DF, Mexico

来源：

SYNTHESIS-STUTTGART | 2024年 / 56卷 / 19期

关键词：

steroids; epimeric lactones; lactols; NMR analysis; X-ray diffraction; STEROIDS;

D O I：

10.1055/a-2338-4149

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A convenient protocol for the synthesis of A-ring lactones derived from cholesterol was developed. A lactone reduction-lactol separation-reoxidation sequence, applied to the inseparable mixture of diastereomeric lactones, allows the production of multigram amounts of each lactone in pure form. The same sequence applied to A-ring lactones derived from diosgenin produced similar results. A detailed NMR characterization of all the obtained lactones is also provided. X-ray diffraction corroborated the structure of the obtained compounds.

引用

页码：3027 / 3036

页数：10

共 31 条

[1] Synthesis, NMR and crystal characterization of dimeric terephthalates derived from epimeric 4,5-seco-cholest-3-yn-5-ols [J].

Alarcon-Manjarrez, Carlos ;

Arcos-Ramos, Rafael ;

Flores Alamo, Marcos ;

Iglesias-Arteaga, Martin A. .

STEROIDS, 2016, 109 :66-72

[2] Stereoselective syntheses of naturally occurring 5,6-dihydropyran-2-ones [J].

Alberto Marco, J. ;

Carda, Miguel ;

Murga, Juan ;

Falomir, Eva .

TETRAHEDRON, 2007, 63 (14) :2929-2958

[3]

[Anonymous], 2013, OXFORD DIFFRACTION

[4] Toad venom bufadienolides and bufotoxins: An updated review [J].

Asrorov, Akmal M. ;

Kayumov, Muzaffar ;

Mukhamedov, Nurkhodja ;

Yashinov, Ansor ;

Mirakhmetova, Ziyoda ;

Huang, Yongzhuo ;

Yili, Abulimiti ;

Aisa, Haji Akber ;

Tashmukhamedov, Mugrajitdin ;

Salikhov, Shavkat ;

Mirzaakhmedov, Sharafitdin .

DRUG DEVELOPMENT RESEARCH, 2023, 84 (05) :815-838

[5] C-13 NMR-STUDIES .69. C-13 NMR-SPECTRA OF STEROIDS - SURVEY AND COMMENTARY [J].

BLUNT, JW ;

STOTHERS, JB .

ORGANIC MAGNETIC RESONANCE, 1977, 9 (08) :439-464

[6] Steroidal lactones as inhibitors of 17β-hydroxysteroid dehydrogenase type 5: Chemical synthesis, enzyme inhibitory activity, and assessment of estrogenic and androgenic activities [J].

Bydal, Patrick ;

Luu-The, Van ;

Labrie, Fernand ;

Poirier, Donald .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2009, 44 (02) :632-644

[7] THE ANALYTICAL CALCULATION OF ABSORPTION IN MULTIFACETED CRYSTALS [J].

CLARK, RC ;

REID, JS .

ACTA CRYSTALLOGRAPHICA SECTION A, 1995, 51 :887-897

[8] GENERAL DEFINITION OF RING PUCKERING COORDINATES [J].

CREMER, D ;

POPLE, JA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (06) :1354-1358

[9] OXIDATION OF CHOLEST-4-EN-3-ONE WITH PERIODATE-PERMANGANATE [J].

EDWARD, JT ;

LUNN, WH ;

PUSKAS, I ;

HOLDER, D .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1961, 39 (03) :599-&

[10] STEREOCHEMICAL STUDIES .2. CONFIGURATIONS OF SOME 4-OXACHOLESTANES [J].

EDWARD, JT ;

MORAND, PF .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1960, 38 (08) :1325-1330

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