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Synthese von (±)-2-Oxo-seychellen und (±)-2-Oxo-4-epi-seychellen (1990)

Spitzner, Dietrich ; Klein, Iris

Weinheim : Wiley-Blackwell

Liebigs Annalen 1990 (1990), S. 63-68

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ISSN: 0170-2041

Keywords: Michael addition, aprotic ; [2 + 2] Addition ; Bicyclo[2.2.2]octanes ; Tricyclo[5.3.1.03,8]undecanes ; Sesquiterpene synthesis ; Chemistry ; Organic Chemistry

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Chemistry and Pharmacology

Notes: 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.

Type of Medium: Electronic Resource

URL: http://dx.doi.org/10.1002/jlac.199019900110

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