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2005
Bridged compounds
Q 0060
Palladium Catalyzed Arylation Reactions of meta Photocycloadducts. —
Heck-like arylation reaction is performed on meta photocycloadducts yielding the
04- 082 The
desired arylation adducts. The methoxy group of anisole (I) directs meta addition of the
allyl alcohol (II) across the 2,6-positions of the aromatic ring during the photo reaction
affording four photocycloadducts, with the desired endo-isomer (III) being easily separable from the mixture. Arylation of (III) introduces the aryl group onto the exo face
of the bridged bicyclic ring. In just two operations a significant portion of the gelsemine
skeleton is assembled, as exemplified with (VIII). The arylation/fragmentation reaction
is applied to a simple alkylbenzene-derived meta photocycloadduct, the 7-endo isomer
(XII). — (PENKETT*, C. S.; SIMS, R. O.; FRENCH, R.; DRAY, L.; ROOME, S. J.;
HITCHCOCK, P. B.; Chem. Commun. (Cambridge) 2004, 17, 1932-1933; Dep.
Chem., Univ. Sussex, Brighton BN1 9QJ, UK; Eng.) — H. Hoennerscheid
2005
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