Toward a total synthesis of amphidinolide N: convergent synthesis of the C1–C13 segment. Issue 31 (3rd August 2016)

• Record Type: Journal Article
• Authors: Toyoshima, Atsushi; Sasaki, Makoto
• Is Part Of: Tetrahedron letters. Volume 57:Issue 31(2016)
• Page Start: 3532
• Page End: 3534
• Publication Date: 2016-08-03
• Subjects: Amphidinolide N -- Cytotoxic macrolide -- Convergent synthesis -- Aldol reaction; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2016.06.107
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: The C1–C13 segment of amphidinolide N was synthesized. Vinylogous Mukaiyama and Evans aldol reactions were used to form the requisite two fragments. Convergent union of the two fragments was realized by an aldol reaction. Abstract: A convergent synthesis of the C1–C13 segment of amphidinolide N, a potent cytotoxic marine macrolide isolated from the dinoflagellate Amphidinium sp., was achieved. The key features of the synthesis involve vinylogous Mukaiyama and Evans aldol reactions to form the C1–C7 and C8–C13 fragments, and convergent union of the two fragments by means of an aldol reaction to construct the C1–C13 segment.