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Total Synthesis of Potent Antifungal Marine Bisoxazole Natural Products Bengazoles A and B

✍ Scribed by James A. Bull; Emily P. Balskus; Richard A. J. Horan; Martin Langner; Steven V. Ley

Publisher
John Wiley and Sons
Year
2007
Tongue
English
Weight
479 KB
Volume
13
Category
Article
ISSN
0947-6539

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✦ Synopsis

Abstract

The bengazoles are a family of marine natural products that display potent antifungal activity and a unique structure, containing two oxazole rings flanking a single carbon atom. Total syntheses of bengazole A and B are described, which contain a sensitive stereogenic centre at this position between the two oxazoles. Additionally, the synthesis of 10‐epi‐bengazole A is reported. Two parallel synthetic routes were investigated, relying on construction of the 2,4‐disubstituted oxazole under mild conditions and a diastereoselective 1,3‐dipolar cycloaddition. Our successful route is high yielding, provides rapid access to single stereoisomers of the complex natural products and allows the synthesis of analogues for biological evaluation.

📜 SIMILAR VOLUMES

Stereocontrolled Total Synthesis of Beng
Stereocontrolled Total Synthesis of Bengazole A: A Marine Bisoxazole Natural Product Displaying Potent Antifungal Properties.
✍ James A. Bull; Emily P. Balskus; Richard A. J. Horan; Martin Langner; Steven V. 📂 Article 📅 2007 🏛 John Wiley and Sons ⚖ 14 KB

## Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract, please click on HTML or PDF.

ChemInform Abstract: Total Synthesis of
ChemInform Abstract: Total Synthesis of the Potent Antifungal Agents Bengazole C and E.
✍ Alvaro Enriquez-Garcia; Steven V. Ley 📂 Article 📅 2009 🏛 John Wiley and Sons ⚖ 25 KB

## Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable v