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Stereoselective Synthesis of Donor−Acceptor Substituted Cyclopropafuranones by Intramolecular Cyclopropanation of Vinylogous Carbonates: Divergent Synthesis of Tetrahydrofuran-3-one, Tetrahydropyran-3-one, and Lactones

✍ Scribed by Gharpure, Santosh J.; Shukla, Manoj K.; Vijayasree, U.


Book ID
118210955
Publisher
American Chemical Society
Year
2009
Tongue
English
Weight
208 KB
Volume
11
Category
Article
ISSN
1523-7060

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A short stereoselective synthesis of (+)
✍ Michael P Doyle; Arthur J Catino 📂 Article 📅 2003 🏛 Elsevier Science 🌐 English ⚖ 114 KB

The synthesis of (1S,5R)-(-)-2-oxabicyclo[3.3.0]oct-6-en-3-one, a useful synthetic precursor en route to various prostaglandins, from divinylcarbinol via catalytic metathesis and C H insertion of 3-cyclopentenyl diazoacetate is described. Enantioselectivities of 90±1% have been achieved in the inser