Stereoselective Synthesis of the Butyrolactone and the Oxazoline/Furan Fragment of Leupyrrin A1

Stereoselective syntheses of the Northern and the Southern fragments 2 and 3 of leupyrrin A1 are reported. The convergent preparation of 2 is highlighted by a zirconocene-mediated one-pot cyclization–regioselective opening of an advanced diyne while the route to 3 involves a Krische allylation and a...

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Bibliographic Details
Published in:Organic letters 2013-06, Vol.15 (11), p.2774-2777
Main Authors: Debnar, Thomas, Wang, Tongtong, Menche, Dirk
Format: Article
Language:English
Online Access:Get full text
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Summary:Stereoselective syntheses of the Northern and the Southern fragments 2 and 3 of leupyrrin A1 are reported. The convergent preparation of 2 is highlighted by a zirconocene-mediated one-pot cyclization–regioselective opening of an advanced diyne while the route to 3 involves a Krische allylation and a one-pot Sharpless dihydroxylation–cyclization. Comparison of the spectroscopic data with those reported for the natural product supports a relative stereochemical assignment within these heterocycles.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol401110x