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Stereoselective Synthesis of [3.3.0]-Fused γ-Butyrolactones of Carbohydrates.

✍ Scribed by Ramon Alibes; Jose Luis Bourdelande; Anna Gregori; Josep Font; Albert Rustullet; Teodor Parella

Publisher
John Wiley and Sons
Year
2004
Weight
107 KB
Volume
35
Category
Article
ISSN
0931-7597

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Facile and stereoselective synthesis of
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Photocycloadducts obtained from different homochiral butenolides and vinylene carbonate are shown to be useful precursors of fused "f-butyrolactones of carbohydrates. @ 1998 Elsevier Science Ltd. All rights reserved.

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Stereoselective rearrangement of 6,7-epoxy-3-oxabicyclo[3.2.0]heptan-2-ones 2 and 3 in water afforded a cisfused butyrolactone as a mixture of two epimers 1a-b. These were used as the starting materials to prepare new bicyclonucleosides 8a-b.