Towards the total synthesis of the anti-trypanosomal macrolide, Actinoallolides: construction of a key linear intermediate. Issue 3 (20th January 2016)

• Record Type: Journal Article
• Authors: Oshita, Jun; Noguchi, Yoshihiko; Watanabe, Akito; Sennari, Goh; Sato, Shogo; Hirose, Tomoyasu; Oikawa, Daiki; Inahashi, Yuki; Iwatsuki, Masato; Ishiyama, Aki; Ōmura, Satoshi; Sunazuka, Toshiaki
• Is Part Of: Tetrahedron letters. Volume 57:Issue 3(2016)
• Page Start: 357
• Page End: 360
• Publication Date: 2016-01-20
• Subjects: 12-Membered macrolide -- Physicochemical screening -- Stereo-divergent synthesis -- Kinetic resolution -- Hartwig's arylation Krische's crotylation; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2015.12.022
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Abstract: Herein, we describe the synthesis of key intermediate (+)-8 as an essential intermediate including full carbon framework for completing the convergent total synthesis of Actinoallolide A (1 ). (+)-8 was obtained by Negishi and Stille cross coupling from (+)-9, (+)-10 and (−)-11 . Stereo-divergent preparation of two similar units, consisting of three consecutive stereocenters, facilitated the synthesis of (+)-10 and (−)-11 .