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Synthese von (±)‐2‐Oxo‐seychellen und (±)‐2‐Oxo‐4‐ epi ‐seychellen
Author(s) -
Spitzner Dietrich,
Klein Iris
Publication year - 1990
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.199019900110
Subject(s) - chemistry , diastereomer , epimer , octane , adduct , bicyclic molecule , lithium (medication) , michael reaction , stereochemistry , medicinal chemistry , organic chemistry , catalysis , medicine , endocrinology
Synthesis of (±)‐2‐Oxo‐seychellene and (±)‐2‐Oxo‐4‐ epi ‐seychellene Aprotic 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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