A General Solution to the Modular Synthesis of Polyketide Building Blocks by Kanemasa Hydroxy-Directed Nitrile Oxide Cycloadditions

Jeffrey W Bode; Nina Fraefel; Dieter Muri; Erick M Carreira

doi:10.1002/1521-3773(20010601)40:11<2082::AID-ANIE2082>3.0.CO;2-1

A General Solution to the Modular Synthesis of Polyketide Building Blocks by Kanemasa Hydroxy-Directed Nitrile Oxide Cycloadditions

Angew Chem Int Ed Engl. 2001 Jun 1;40(11):2082-2085. doi: 10.1002/1521-3773(20010601)40:11<2082::AID-ANIE2082>3.0.CO;2-1.

Authors

Jeffrey W Bode¹, Nina Fraefel¹, Dieter Muri¹, Erick M Carreira¹

Affiliation

¹ Laboratorium für Organische Chemie ETH-Zentrum Universitätstrasse 16, 8092 Zürich (Switzerland) Fax: (+41) 1-632-13-28.

PMID: 29712193
DOI: 10.1002/1521-3773(20010601)40:11<2082::AID-ANIE2082>3.0.CO;2-1

Abstract

A single, convenient reaction protocol and the same set of readily available starting materials suffice for the modular synthesis of all possible polypropionate diastereomers. This general method for the diastereoselective synthesis of syn, anti, and methyl ketone aldol adducts utilizes a powerful Mg^II -mediated, hydroxy-directed nitrile oxide cycloaddition. The free hydroxy group provides an ideal synthetic handle enabling the rapid assembly of complex polyketide structures. TBS=tBuMe₂ Si.

Keywords: aldol reaction; cycloaddition; erythronolides; polyketides.