A synthetic approach to the phorboxazoles - A strategy for the synthesis of the C1-C19 polyketide fragment

TETRAHEDRON LETTERS

卷:59

Article

Leahy, James W.^1,2,3  Carroll, David C.⁴  McElhone, Kate E.⁴ 

[1] Univ S Florida, Dept Chem, CHE 205,4202 E Fowler Ave, Tampa, FL 33620 USA

[2] Univ S Florida, Florida Ctr Excellence Drug Discovery & Innovat, 3720 Spectrum Blvd,Suite 303, Tampa, FL 33612 USA

[3] Univ S Florida, Morsani Coll Med, Dept Mol Med, MDC 7,12901 Bruce B Downs Blvd, Tampa, FL 33612 USA

[4] Univ Calif Berkeley, Dept Chem, Berkeley, CA 94720 USA

关键词: Phorboxazoles;    Total synthesis;    Two-directional synthesis;   

DOI  :  10.1016/j.tetlet.2017.12.007

来源: Elsevier

【 摘 要 】

A synthetic approach to the C1-C19 polyketide fragment of the phorboxazoles is disclosed here. While an initial two-directional approach was efficient, it did not proceed in a high enough yield to justify moving forward. A subsequent successful strategy for the generation of the C11-C15 pyrans of both of the phorboxazoles was achieved, and the installation of the C9 stereocenter was able to be demonstrated. Furthermore, an efficient route for the preparation of the C1-C8 fragment with suitable functionality to allow for elaboration into the complete C1-C19 fragment, with the capricious C2-C3 Z-geometry installed, was also achieved. (C) 2017 Elsevier Ltd. All rights reserved.

【 授权许可】

Free