Total synthesis of (-)-haploscleridamine

TETRAHEDRON LETTERS

卷:60

Article

Roy, Moumita Singha¹  Meng, Xiaofeng¹  Koda, Karuna¹  Rasapalli, Sivappa²  Gout, Delphine³  Lovely, Carl J.¹ 

[1] Univ Texas Arlington, Dept Chem & Biochem, 700 Planetarium Pl, Arlington, TX 76019 USA

[2] Univ Massachusetts, Dept Chem & Biochem, 285 Old Westport Rd, Dartmouth, MA 02747 USA

[3] Univ Texas Arlington, Ctr Nanostruct Mat, 700 Planetarium Pl, Arlington, TX 76019 USA

关键词: beta-Carboline;    Ring closing metathesis;    Fischer indole synthesis;    Chiral pool;   

DOI  :  10.1016/j.tetlet.2019.03.004

来源: Elsevier

【 摘 要 】

Asymmetric total synthesis of the imidazole containing beta-carboline natural product, haploscleridamine, from histidine is described. Key to the successful assembly of this alkaloid is a ring-closing metathesis reaction of an imidazole derived allylic alcohol to construct a 3-piperidinone. Application of the Buchwald-modification of the classical Fischer indolization and deprotection of the N-tosyl moiety delivered haploscleridamine. (C) 2019 Published by Elsevier Ltd.

【 授权许可】

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