Synthesis 2015; 47(18): 2709-2712
DOI: 10.1055/s-0034-1378822
psp
© Georg Thieme Verlag Stuttgart · New York

An Efficient Directed Claisen Reaction Allows for Rapid Construction of 5,6-Disubstituted 1,3-Dioxin-4-ones

Ziyang Zhang
Department of Chemistry and Chemical Biology, Harvard University, Cambridge, MA 02138, USA   Email: [email protected]
,
Yoshiaki Kitamura
Department of Chemistry and Chemical Biology, Harvard University, Cambridge, MA 02138, USA   Email: [email protected]
,
Andrew G. Myers*
Department of Chemistry and Chemical Biology, Harvard University, Cambridge, MA 02138, USA   Email: [email protected]
› Author Affiliations
Further Information

Publication History

Received: 01 July 2015

Accepted after revision: 09 July 2015

Publication Date:
03 August 2015 (online)


Abstract

An efficient directed Claisen reaction between tert-butyl propionate and phenyl propionate is described. This enables a practical synthesis of 6-ethyl-2,2,5-trimethyl-4H-1,3-dioxin-4-one and thereby (Z)-[(4-ethylidene-2,2,5-trimethyl-4H-1,3-dioxin-6-yl)oxy]trimethylsilane, a key building block in our synthesis of macrolide antibiotics. The three-step route elaborated for the preparation of the latter substance requires no chromatography and is amenable to large-scale synthesis.

 
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