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Synthesis of Medium and Large Rings, XLIV. Synthesis of Optically Active Bridged Bicyclobutane Derivatives

✍ Scribed by Tochtermann, Werner ;Panitzsch, Torsten ;Peschanel, Matthias ;Wolff, Christian ;Peters, Eva-Maria ;Peters, Karl ;von Schnering, Hans Georg

Publisher
John Wiley and Sons
Year
1997
Tongue
English
Weight
533 KB
Volume
1997
Category
Article
ISSN
0947-3440

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✦ Synopsis

Abstract

Irradiation of the dihydrooxepine monoester (+)‐4 gives the bridged bicyclobutane (+)‐5 in 77% yield. On the other hand, the corresponding diester 1 yields the cyclobutene 2. Possible explanations for this differing behaviour are discussed.

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Treatment of the bridged methyl furanosides 1, 3 and 5 with dilute acid furnishes the corresponding deoxyfuranose derivatives 2, 4 and 6. The trans-substitution pattern of the tetrahydrofuran ring was established by X-ray structural analysis of 2 and by comparison of the 1 H-NMR spectra. A new reso-