Total synthesis of the proposed structure of astakolactin

Takayuki Tonoi; Keisuke Mameda; Moe Fujishiro; Yutaka Yoshinaga; Isamu Shiina

doi:10.3762/bjoc.10.252

Total synthesis of the proposed structure of astakolactin

Beilstein J Org Chem. 2014 Oct 17:10:2421-7. doi: 10.3762/bjoc.10.252. eCollection 2014.

Authors

Takayuki Tonoi¹, Keisuke Mameda¹, Moe Fujishiro¹, Yutaka Yoshinaga¹, Isamu Shiina¹

Affiliation

¹ Department of Applied Chemistry, Tokyo University of Science,1-3 Kagurazaka, Shinjuku-ku, Tokyo 162-8601, Japan.

Abstract

The first total synthesis of the proposed structure of astakolactin, a sesterterpene metabolite isolated from the marine sponge Cacospongia scalaris, has been achieved, mainly featuring Johnson-Claisen rearrangement, asymmetric Mukaiyama aldol reaction and MNBA-mediated lactonization.

Keywords: MNBA; aldol reaction; astakolactin; lactonization; terpenoids.