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Synthesis 2005(14): 2421-2425
DOI: 10.1055/s-2005-870018
DOI: 10.1055/s-2005-870018
PAPER
© Georg Thieme Verlag Stuttgart · New York
An Efficient Synthesis of Carlosic Acid and Other 5-Carboxymethyltetronates from Malates
Further Information
Received
16 March 2005
Publication Date:
14 July 2005 (online)
Publication History
Publication Date:
14 July 2005 (online)
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Abstract
S-Carlosic acid was prepared in six steps and 32% yield from malic acid. Ring closure was effected by a domino addition-Wittig alkenation reaction with Ph3PCCO. A variant employing resin-bound malates furnished immobilized 5-carboxymethyltetronates. It should be amenable to parallelization and automation.
Key words
domino reactions - solid-phase - lactones - natural products - bismuth triflate
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