Michael addition, aprotic
[2 + 2] Addition
Wiley InterScience Backfile Collection 1832-2000
Chemistry and Pharmacology
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.
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