Total synthesis of brevenal

TETRAHEDRON

卷:66

Article

Takamura, Hiroyoshi¹  Yamagami, Yuji¹  Kishi, Takayuki¹  Kikuchi, Shigetoshi²  Nakamura, Yuichi¹  Kadota, Isao¹  Yamamoto, Yoshinori² 

[1] Okayama Univ, Dept Chem, Grad Sch Nat Sci & Technol, Kita Ku, Okayama 7008530, Japan

[2] Toho Univ, Grad Sch Sci, Dept Chem, Sendai, Miyagi 9808578, Japan

关键词: Brevenal;    Marine polycyclic ether;    Total synthesis;    Intramolecular allylation;    Ring-closing metathesis;   

DOI  :  10.1016/j.tet.2010.05.069

来源: Elsevier

【 摘 要 】

The convergent total synthesis of brevenal, a non-toxic brevetoxin antagonist, has been achieved. The ABC ring segment and the E ring precursor were connected by the intramolecular allylation followed by ring-closing metathesis to furnish the pentacyclic ether compound. An alternative route to the key synthetic intermediate, a pentacyclic ether core, was also examined. The right- and left-hand side chains were introduced by Wittig and Horner-Wadsworth-Emmons reactions, respectively, to furnish brevenal (1). (C) 2010 Elsevier Ltd. All rights reserved.

【 授权许可】

Free