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4 and NMO in THF the fully aromatized silanol 6b was formed as the sole product.
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51
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The enantiomeric excess was determined using capillary GC (Cyclodex-B).
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54
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The 1,2-trans-diaxial epoxide ring opening obeys the Fürst- Plattner rules; see: (a) Fürst, A.; Plattner, P. A. Helv. Chim. Acta 1949, 32, 275. (b) Hudlicky, T.; Rouden, J.; Luna, H.; Allen, S. J. Am. Chem. Soc. 1994, 116, 5099.
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64
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Isolation of (+)-palitantine: Bowden, K.; Lythgoe, B.; Marsden, D. J. S. J. Chem. Soc. 1959, 1662. Total asymmetric syntheses of (+)- palitantine: (a) Deruyttere, X.; Dumortier, L.; Van der Eycken, J.; Vandewalle, M. Synlett 1992, 51. (b) Hanessian, S.; Sakito, Y.; Dhanoa, D.; Baptistella, L. Tetrahedron 1989, 45, 6623.
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Isolation of (+)-palitantine: Bowden, K.; Lythgoe, B.; Marsden, D. J. S. J. Chem. Soc. 1959, 1662. Total asymmetric syntheses of (+)-palitantine: (a) Deruyttere, X.; Dumortier, L.; Van der Eycken, J.; Vandewalle, M. Synlett 1992, 51. (b) Hanessian, S.; Sakito, Y.; Dhanoa, D.; Baptistella, L. Tetrahedron 1989, 45, 6623.
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Isolation of (+)-palitantine: Bowden, K.; Lythgoe, B.; Marsden, D. J. S. J. Chem. Soc. 1959, 1662. Total asymmetric syntheses of (+)- palitantine: (a) Deruyttere, X.; Dumortier, L.; Van der Eycken, J.; Vandewalle, M. Synlett 1992, 51. (b) Hanessian, S.; Sakito, Y.; Dhanoa, D.; Baptistella, L. Tetrahedron 1989, 45, 6623.
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Hydrolysis of the enolate directly after the cupration afforded the addition product as a unique diastereomer having the trans relationship between the acetonide and the dienyl chain at C-3.
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2(O-iPr) (60%) 100 : 0
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