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A Symmetry-Based Synthesis of the Heterobicyclic Core of the Zaragozic Acids/Squalestatins

โœ Scribed by Yuzhou Wang; Olga Kataeva; Peter Metz

Publisher
John Wiley and Sons
Year
2009
Tongue
English
Weight
215 KB
Volume
351
Category
Article
ISSN
1615-4150

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โœฆ Synopsis

Abstract

The pseudo C~2~โ€symmetrical diketone 22 was efficiently constructed from furanโ€3,4โ€dimethanol (7) using a twoโ€directional route featuring a double asymmetric dihydroxylation. Acidic hydrolysis of the cyclopentylidene acetals of 22 triggered a selective cyclization of the resulting hexaol diketone to generate the 2,8โ€dioxabicyclo[3.2.1]octane core of the zaragozic acids/squalestatins. Chemoselective oxidative cleavage of a superfluous twoโ€carbon appendage and further functional group manipulations yielded the enantiomerically pure triester 30, which offers itself as a general heterobicyclic building block for naturally occurring zaragozic acids/squalestatins and unnatural analogues.

๐Ÿ“œ SIMILAR VOLUMES

Total Synthesis of Zaragozic Acid A/Squa
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## Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a โ€œFull Textโ€ option. The original article is trackable v

ChemInform Abstract: Evaluation of Furan
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Evaluation of Furan Photooxygenation as a Device for Construction of the Zaragozic Acid (Squalestatin) Core. -The photooxygenation of compound (IX) allows the stereocontrolled construction of the title core (X) starting from (I) in seven steps. -(MAEZAKI, N.; GIJSEN, H.