Synthesis 2005(19): 3219-3224  
DOI: 10.1055/s-2005-918486
PAPER
© Georg Thieme Verlag Stuttgart · New York

Synthesis of the C14-C28 Fragment of Tetronasin

Elyse Bourquea, Philip J. Kocienski*a, Michael Stocksb, Josephine Yuena
a School of Chemistry, Leeds University, Leeds LS2 9JT, UK
b AstraZeneca R & D Charnwood, Bakewell Road, Loughborough, Leicestershire LE11 5RH, UK
Fax: +44(113)3436401; e-Mail: p.kocienski@chemistry.leeds.ac.uk;
Further Information

Publication History

Received 5 May 2005
Publication Date:
14 November 2005 (online)

Abstract

A synthesis of the C14-C28 fragment of Tetronasin features an SE2 reaction between a cationic η3-allylmolybdenum complex and and an α-metallated tetrahydrofuran.

26

The five- and six-membered lactones were easily distinguished by their characteristic 13C NMR signals for the C=O groups at δ = 178.1 and 171.2, respectively.

32

A pure sample of (23R)-21 could not be obtained; therefore the NOE data was recorded on a mixture enriched in (23R)-21.

34

Compound (23R)-27 is an intermediate in the Yoshii synthesis of Tetronomycin (see ref. 5).