A total synthesis of (-)-hortonone C

TETRAHEDRON

卷:73

Article

Niroula, Doleshwar¹  Hallada, Liam P.^1,2  Rogelj, Snezna²  Tello-Aburto, Rodolfo¹ 

[1] New Mexico Inst Min & Technol, Dept Chem, Socorro, NM 87801 USA

[2] New Mexico Inst Min & Technol, Dept Biol, Socorro, NM 87801 USA

关键词: Hortonones;    Natural products;    Total synthesis;    Asymmetric conjugate addition;    Hydroazulene;    Hydroindane;   

DOI  :  10.1016/j.tet.2016.12.013

来源: Elsevier

【 摘 要 】

A total synthesis of the cytotoxic terpenoid hortonone C was accomplished and its absolute stereo chemistry confirmed. Intermediate (+)-4 was synthesized using either an asymmetric conjugate addition strategy, or by elaboration of the Hajos-Parrish ketone. Reduction of (+)-4 under dissolving-metal conditions and trapping the enolate intermediate served to control the cis-stereochemistry at the ring fusion and provide a silyl enol ether necessary for ring expansion. Comparison of optical rotation data confirmed that the absolute configuration of natural hortonone C is (6S,7S,10S). (C) 2016 Elsevier Ltd. All rights reserved.

【 授权许可】

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