ISSN:
1434-193X
Keywords:
Natural products
;
Intramolecular Diels-Alder reactions
;
2-Siloxycyclopropanecarboxylates
;
1,7,9-Decatrien-3-ones
;
Octalones
;
Chemistry
;
General Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
-Starting from enones 7 and 8 siloxydienes 9 and 12 were synthesized. Cyclopropanation and subsequent alkylation with sorbyl bromide provided tetrasubstituted siloxycyclopropanes 15 and 16 in good overall efficiency. Their ring cleavage with fluoride reagents gave 1,7,9-decatrienones 5 and 17; the latter was converted into the protected compound 6. The thermal intramolecular Diels-Alder reactions of 5 and 6 were compared with those of related trienones 3 and 4. Octalones 1, 2, 21, and 22 were formed as mixtures of three or four diastereomers. Thus, for the stereoselective construction of natural products such as α-eudesmol or dihydromevinolin alternative reaction conditions for the cycloaddition step have to be developed.
Additional Material:
5 Tab.
Type of Medium:
Electronic Resource
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