Work

Search for Highly Efficient, Stereoselective, and Practical Synthesis of Complex Organic Compounds of Medicinal Importance as Exemplified by the Synthesis of the C21C37 Fragment of Amphotericin B

Year: 2013

Type: article

Abstract: Highly stereoselective: A highly efficient, stereoselective and practical synthesis of the C21-C37 fragment of amphotericin B was realized in 25 % overall yield in eight longest linear steps from commercially available ethyl (S)-3-hydroxybutyrate by using Fráter-Seebach alkylation, Brown crotylboration, Negishi coupling, Heck reaction, and Horner-Wadsworth-Emmons (HWE) olefination as key steps (see diagram).

Source: Chemistry - A European Journal

DOI: 10.1002/chem.201302383

Authors: Guangwei Wang, Shiqing Xu, Qian Hu, Fanxing Zeng, Ei‐ichi Negishi

Institution: Purdue University West Lafayette

Language: English

Topic: Organic Chemistry Synthesis Methods

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funders: Purdue University, National Institutes of Health, National Institute of General Medical Sciences

Awards: G1475280282, SYNTHETIC REACTIONS CATALYZED BY TRANSITION METALS