Studies on the Synthesis of Natural Products with Bicyclo[4.4.0]decene Skeleton: Synthesis and Uncatalysed Intramolecular Diels–Alder Reactions of the Decatrienone Substrates

✍ Scribed by Barbara Frey; Jürgen Schnaubelt; Hans-Ulrich Reißig

• Publisher: John Wiley and Sons
• Year: 1999
• Tongue: English
• Weight: 279 KB
• Volume: 1999
• Category: Article
• ISSN: 1434-193X
• DOI: 10.1002/(sici)1099-0690(199906)1999:6<1377::aid-ejoc1377>3.0.co;2-l

✦ Synopsis

9-Decatrien-3-ones / Octalones

Starting from enones 7 and 8 siloxydienes 9 and 12 were 6 were compared with those of related trienones 3 and 4.

Octalones 1, 2, 21, and 22 were formed as mixtures of three synthesized. Cyclopropanation and subsequent alkylation with sorbyl bromide provided tetrasubstituted siloxy-or four diastereomers. Thus, for the stereoselective construction of natural products such as α-eudesmol or cyclopropanes 15 and 16 in good overall efficiency. Their ring cleavage with fluoride reagents gave 1,7,9-decatrienones 5 dihydromevinolin alternative reaction conditions for the cycloaddition step have to be developed. and 17; the latter was converted into the protected compound 6. The thermal intramolecular Diels-Alder reactions of 5 and