Total Synthesis of (−)‐Caprazamycin A1. Issue 10 (22nd January 2015)

• Record Type: Journal Article
• Authors: Nakamura, Hugh; Tsukano, Chihiro; Yasui, Motohiro; Yokouchi, Shinsuke; Igarashi, Masayuki; Takemoto, Yoshiji
• Is Part Of: Angewandte Chemie international edition. Volume 54:Issue 10(2015)
• Page Start: 3136
• Page End: 3139
• Publication Date: 2015-01-22
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201411954
• Languages: English
• ISSNs: 1433-7851

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>Caprazamycin A has significant antibacterial activity against Mycobacterium tuberculosis (TB). The first total synthesis is herein reported and features a) the scalable preparation of the <italic>syn</italic>‐β‐hydroxy amino acid with a thiourea‐catalyzed diastereoselective aldol reaction, b) construction of a diazepanone with an unstable fatty‐acid side chain, and c) global deprotection with hydrogenation. This report provides a route for the synthesis of related liponucleoside antibiotics with fatty‐acid side chains.</p> </abstract>