Sulfone mediated synthesis of cyclopentadienone epoxides from 10-oxatricyclo[5.2.1.02,6]decadienones. A convenient route to epi-pentenomycins
✍ Scribed by A.J.H. Klunder; A.A.M. Houwen-Claassen; M.G. Kooy; B. Zwanenburg
- Publisher
- Elsevier Science
- Year
- 1987
- Tongue
- French
- Weight
- 247 KB
- Volume
- 28
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
Sulfonylmethylation of IO-oxatricyclodecadienone 6 leads to sulfone 4 which forms the key intermediate in the synthesis of 5-alkoxymethylcyclopentadienons epoxides 5. Acid catalyzed hydrolysis of 5 followed by acylation affords epi-pentenomycin derivatives 15 Tricyclo[5.2.1.02"]decadienones 1 have great potential as synthetic equivalents of cyclopentadienone and serve as building blocks in cyclopentanoid natural product synthesis. E.g., stereoselective chemical transformation of the enone moiety in 1, followed by thermal cycloreversion, produces functionalized cyclopentenones. Based on this strategy
we recently reported the total synthesis of (+)terrein' and (f)pentenomycin'.