The Stereoselective Total Synthesis of the Elusive Cephalosporolide F

被引：1

作者：

Xochicale-Santana, Leonardo ^{[1
,2
]}

Cortezano-Arellano, Omar ^{[3
]}

Frontana-Uribe, Bernardo A. ^{[4
,5
]}

Jimenez-Perez, Victor M. ^{[2
]}

Sartillo-Piscil, Fernando ^{[1
]}

机构：

[1] Benemerita Univ Autonoma Puebla BUAP, Ctr Invest, Fac Ciencias Quim, Puebla 72570, Mexico

[2] Univ Autonoma Nuevo Leon, Fac Ciencias Quim, San Nicolas De Los Garza 66541, Nuevo Leon, Mexico

[3] Univ Veracruzana, Inst Ciencias Basicas, Xalapa 91190, Veracruz, Mexico

[4] Univ Nacl Autonoma Mexico, Ctr Conjunto Invest Quim Sustentable UAEMex, Mexico City 50200, Estado De Mexic, Mexico

[5] Univ Nacl Autonoma Mexico, Inst Quim, Mexico City 04510, Mexico

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 88卷 / 07期

关键词：

ENANTIOSELECTIVE SYNTHESIS; NATURAL-PRODUCTS; RADICAL CATIONS; MELDRUMS ACID; C-10; LACTONES; CHEMISTRY; GENERATION; PRECURSOR;

D O I：

10.1021/acs.joc.3c00251

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Here we report a seven-step protecting-group-free stereoselective total synthesis of the elusive (+)-cephalosporolide F from D-glucose. A microwave-assisted reaction between the Meldrum's acid and the D-glucose to the respective octono-1,4-lactone derivative, and a low temperature visible-light photoredox spirocyclization of a chiral N-alkoxyphthalimide to ceph F, are the two key chemical reactions that allowed the accomplishment of this unprecedented feat under an environmentally friendly processes.

引用

页码：4880 / 4885

页数：6

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