Helvetica Chimica Acta p. 570 - 593 (1989)
Update date:2022-08-03
Topics:
Snowden, Roger L.
Brauchli, Robert
Sonnay, Philippe
The transformation of 12 bicyclo<2.2.2>oct-5-en-2-ols (V or VI) to 3-(cyclohex-3-enyl)-2-alkanones (III or IV), via β-cleavage of their potassium alkoxides in HMPA, has been investigated (cf. table I).As an illustration of this synthetic methodology, a stereoselective synthesis of (+)-trichodiene ((+)-1) is described wich involves the β-cleavage of the tricyclic potassium alkoxides 46a and 47a to cyclopentanone 4 (cf.Scheme 7).
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