ISSN:
0170-2041
Schlagwort(e):
Michael addition, aprotic
;
[2 + 2] Addition
;
Bicyclo[2.2.2]octanes
;
Tricyclo[5.3.1.03,8]undecanes
;
Sesquiterpene synthesis
;
Chemistry
;
Organic Chemistry
Quelle:
Wiley InterScience Backfile Collection 1832-2000
Thema:
Chemie und Pharmazie
Notizen:
Synthesis of (±)-2-Oxo-seychellene and (±)-2-Oxo-4-epi-seychelleneAprotic Michael additions, which generate the functionalized bicyclo[2.2.2]octane 8 from ethyl 2-methyl-2,3-butadienoate (10) and the lithium cyclohexadienolate 9a, are the key steps in the synthesis of 6 (and its 4-epimer). 6 was made from 8 in 10 steps. The alternative Diels-Alder reaction of 10 with the trimethylsiloxycyclohexadiene 9b gave exclusively the [2+2] adduct 14 as a 1:1 mixture of diastereomers.
Materialart:
Digitale Medien
URL:
http://dx.doi.org/10.1002/jlac.199019900110
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