Synthetic Studies toward the C14-C29 Fragment of Mirabalin

Johan Cornil; Pierre-Georges Echeverria; Sébastien Reymond; Phannarath Phansavath; Virginie Ratovelomanana-Vidal; Amandine Guérinot; Janine Cossy

doi:10.1021/acs.orglett.6b02162

Synthetic Studies toward the C14-C29 Fragment of Mirabalin

Org Lett. 2016 Sep 16;18(18):4534-7. doi: 10.1021/acs.orglett.6b02162. Epub 2016 Sep 7.

Authors

Johan Cornil¹, Pierre-Georges Echeverria², Sébastien Reymond¹, Phannarath Phansavath², Virginie Ratovelomanana-Vidal², Amandine Guérinot¹, Janine Cossy¹

Affiliations

¹ Laboratoire de Chimie Organique, Institute of Chemistry, Biology and Innovation (CBI)-UMR 8231, ESPCI Paris/CNRS/PSL Research University , 10 rue Vauquelin 75231 Cedex 05 Paris, France.
² PSL Research University, Chimie ParisTech - CNRS, Institut de Recherche de Chimie Paris , 75005 Paris, France.

PMID: 27602486
DOI: 10.1021/acs.orglett.6b02162

Abstract

A convergent synthesis of one isomer of the C14-C29 fragment of mirabalin is disclosed. The key steps include a Marshall allenylation, a Mukaiyama aldol reaction and a Crimmins aldolization, which allow the control of 10 out of 25 stereogenic centers present in the molecule.

Publication types

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