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Synthesis 2008(4): 589-593  
DOI: 10.1055/s-2008-1032145
PAPER
© Georg Thieme Verlag Stuttgart · New York

DBU/Et3N-Mediated Sequential Homoaldol-Lactonization-Alkylation Reactions of Ethyl Pyruvate: One-Pot Synthesis of O-Protected Isotetronic Acids

Yuzhu Sun, Huansheng Chen, Zhiming Li, Quanrui Wang*, Fenggang Tao
Department of Chemistry, Fudan University, 200433 Shanghai, P. R. of China
Fax: +86(21)65641740; e-Mail: qrwang@fudan.edu.cn;
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Publication History

Received 18 October 2007
Publication Date:
31 January 2008 (online)

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Abstract

The sequential homoaldol-lactonization-alkylation/acylation­ reactions of ethyl pyruvate with a variety of halides were achieved by using DBU along with Et3N as the base. The protocol provides an expedient one-pot synthesis of O-protected isotetronic acid derivatives. The high-yielding synthesis of an unprotected isotetronic acid is also described.

Key words

pyruvate - aldol reactions - one-pot reactions - isotetronic acids

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