Work

Enantioselective Syntheses of (–)‐Alloyohimbane and (–)‐Yohimbane by an Efficient Enzymatic Desymmetrization Process

Year: 2016

Type: article

Abstract: Enantioselective syntheses of (–)‐alloyohimbane and (–)‐yohimbane were accomplished in a convergent manner. The key step involves a modified mild protocol for the enantioselective enzymatic desymmetrization of a meso‐diacetate. This provides convenient access to an optically active monoacetate in multi‐gram quantities and in high enantiomeric purity. This monoacetate was converted to (–)‐alloyohimbane. Reductive amination of the derived aldehyde caused isomerization to the trans‐product and, ultimately, the formation of (–)‐yohimbane.

Source: European Journal of Organic Chemistry

DOI: 10.1002/ejoc.201601171

Authors: Arun K. Ghosh, Anindya Sarkar

Institution: Purdue University West Lafayette

Language: English

Topic: Advanced Synthetic Organic Chemistry

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funder: National Institute of General Medical Sciences

Awards: G1202569080, Design & Synthesis of Nonpeptide Protease Inhibitors