Work

Total Synthesis of Aplyronine C

Year: 2013

Type: article

Abstract: A highly stereocontrolled total synthesis of the cytotoxic marine macrolide aplyronine C is described. The route exploits aldol methodology to install the requisite stereochemistry and features a crucial boron-mediated aldol coupling of an N-vinylformamide-bearing methyl ketone with a macrocyclic aldehyde to introduce the full side chain. The synthesis of two novel C21-C34 side chain analogs is also reported.

Source: Organic Letters

DOI: 10.1021/ol401327r

Authors: Ian Paterson, Sarah J. Fink, Lydia Y. W. Lee, Stephen J. Atkinson, Simon B. Blakey

Institution: University of Cambridge

Language: English

Topic: Advanced Synthetic Organic Chemistry

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $4,500

Funders: Williams College, Swansea University, Croucher Foundation, Engineering and Physical Sciences Research Council