Total synthesis of sparstolonin B via a palladium-catalyzed aldehyde α-arylation

TETRAHEDRON

卷:74

Article

Kim, Dalton¹  Nash, Aaron²  De Brabander, Jef, Jr.²  Tambar, Uttam K.² 

[1] Northwestern Univ, Dept Chem, 2145 Sheridan Rd, Evanston, IL 60208 USA

[2] Univ Texas Southwestern Med Ctr Dallas, Dept Biochem, 5323 Harry Hines Blvd, Dallas, TX 75390 USA

关键词: Palladium catalysis;    Arylation;    Total synthesis;    Autoredox;    Cross-coupling;   

DOI  :  10.1016/j.tet.2018.05.012

来源: Elsevier

【 摘 要 】

A concise and convergent total synthesis of sparstolonin B was developed. A palladium-catalyzed aldehyde alpha-arylation was utilized to construct the carbon skeleton of the natural product. A subsequent simple one-pot procedure effected global deprotection and closure of the final two rings via an unusual autoredox mechanism for the conversion of a bis-hydroquinone intermediate to the natural product. The 6 step synthetic sequence was realized in 18% overall yield. (C) 2018 Elsevier Ltd. All rights reserved.

【 授权许可】

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