Studies towards a biomimetic synthesis of α-cyclopiazonic acid: Synthesis of 5-substituted isoxazole-4-carboxylic esters

V Moorthie, EM McGarrigle, R Stenson, VK Aggarwal

Research output: Contribution to journalArticle (Academic Journal)peer-review

4 Citations (Scopus)

Abstract

An efficient, high yielding synthesis of ethyl 5-hydroxymethyl-3-methylisoxazole-4-carboxylate has been developed, based on a procedure by Gelin which involves reaction of ethyl acetoacetate with chloroacetyl chloride followed by treatment with hydroxylamine hydrochloride. The product of this reaction was then converted into the bromide and reacted with tetrahydrothiophene to give sulfonium salts in up to 71% overall yield (from ethyl acetoacetate). The synthesis is suitable for use with a chiral sulfide and for large-scale use. The synthesis of ethyl 5-formyl-3-methyl-4-isoxazolecarboxylate and the corresponding tosylhydrazone are also reported. These isoxazoles are starting materials for a proposed convergent, biomimetic synthesis of α-cyclopiazonic acid.
Translated title of the contributionStudies towards a biomimetic synthesis of α-cyclopiazonic acid: Synthesis of 5-substituted isoxazole-4-carboxylic esters
Original languageEnglish
Pages (from-to)139 - 151
Number of pages13
JournalArkivoc
Volume2007 (v)
Publication statusPublished - Jun 2007

Bibliographical note

Publisher: ARKAT USA Inc

Fingerprint Dive into the research topics of 'Studies towards a biomimetic synthesis of α-cyclopiazonic acid: Synthesis of 5-substituted isoxazole-4-carboxylic esters'. Together they form a unique fingerprint.

Cite this