ISSN:
0170-2041
Keywords:
Stereum purpureum
;
Cuprates, organo-
;
1,6-Addition
;
Vinylallenes
;
Diels-Alder reaction, intramolecular
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The synthesis of (±)-sterpurene (1), 14-/15-hydroxysterpurene (13), and 11,14-/11,15-dihydroxysterpurene (14) is described. Key steps are the 1,6-addition of lithium dimethylcuprate to the 2-en-4-ynoate 11 and the regioselective trapping of the allenyl enolate with methyl triflate. The vinylallene 6 thus obtained undergoes an intramolecular Diels-Alder reaction to give the tricyclic ester 5, which serves as a common precursor of 1, 13, and 14.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.199319930186
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