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Synthesis of spiro-sesquiterpenes in the vetivane series via an aza-claisen rearrangement

✍ Scribed by Patrick M. McCurry Jr.; Rajendra K. Singh

Publisher: Elsevier Science
Year: 1973
Tongue: French
Weight: 181 KB
Volume: 14
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)86906-9

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✦ Synopsis

We wish to report a version of the aae&Xaisen rearrangement1 whioh should prove useful in the preparation of dlastereomerio apiro oompounds. Speoifioally, we have applied this method in the total syntheeis of Spiro-sesquiterpenee (i-) S-vet&one (Ia)? (+) 10-epi-0-vetivone2b( Ib), and (k) R-vetiapirene3 (II). Ib Camphooeenio aldehyde' (III) [b.p. 8S-92' at 13 mm; nmr 1.60 (6H), 9.40 (lH, d,J = 1.5 Hz)], obtained in 46% yield from oamphoceenia nItrile, by reduotion vith diisobutyl aluminum hydride at O", was converted to the triaubstituted pyrrolidine enamlne IV [97% yield, b.p. 78-80' at 0.1 mm; nmr 1.61 (6H), 5.70 (ml J.

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