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Diastereoselective Formal Synthesis of the Antifungal Agent, (+)-Preussin. A New Entry to Chiral Pyrrolidines

✍ Scribed by Pedro de Armas; Fernando García-Tellado; José J. Marrero-Tellado; Juana Robles

Book ID: 104258440
Publisher: Elsevier Science
Year: 1998
Tongue: French
Weight: 520 KB
Volume: 39
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(97)10468-3

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✦ Synopsis

Received15September 1997; revised23October1997; accepted24October1997 Abs!mct:A formaltotal synthesisof (+)-preussinwas achieved by using D mannoseas the starting material. The key step involveddiasteremelective additionof ailyltrimethylsilane to the bicyclicketrd5. @1997Elsevicr ScienceLtd. Ml nghti reserved.

The potentantifungalantibiotic(+)%ewsin (L-675S%3)1, has ban isolatedfrom the microorganisms Preussiasp andAspergit'fus ochraceusATCC 22947.'

Due to its interestingactivities, to the best of 'dur knowledgesix total syntheses of 1 have been described.zThesestrategiesemploydifferentproceduresfor the installationof the R cotilguration of the C5 nonyl side chain.

Herewe describea diastereoselectiveformalsynthesisof (+)-preussin. Our syntheticstrategyis outlined in Scheme 1.

Aekmewlsd@mse-This*ork was suppmtedby the SpanishIXHCYT(PB9MW28 ). JRc thanksthe la f~a ~1 fd~wship.

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