Total synthesis of apratoxin A

Takayuki Doi; Yoshitaka Numajiri; Asami Munakata; Takashi Takahashi

doi:10.1021/ol052907d

Total synthesis of apratoxin A

Org Lett. 2006 Feb 2;8(3):531-4. doi: 10.1021/ol052907d.

Authors

Takayuki Doi¹, Yoshitaka Numajiri, Asami Munakata, Takashi Takahashi

Affiliation

¹ Department of Applied Chemistry, Tokyo Institute of Technology, 2-12-1, Ookayama, Meguro, Tokyo 152-8552, Japan. [email protected]

PMID: 16435877
DOI: 10.1021/ol052907d

Abstract

[reaction: see text]. We have achieved a total synthesis of apratoxin A in which thiazoline formation was accomplished from the moCys containing amide 4 using PPh3(O)/Tf2O. Deprotection of the Troc and allyl ester in 17, coupling with tripeptide 3, and deprotection of the allyl ester and the Fmoc, followed by macrolactamization provided apratoxin A (1).

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Cyanobacteria / chemistry
Depsipeptides / chemical synthesis*
Depsipeptides / chemistry
Molecular Structure
Thiazoles / chemistry*

Substances

Depsipeptides
Thiazoles
apratoxin A