Synthesis of the C26-C32 Oxazole Fragment of Calyculin C: A Test Case for Oxazole Syntheses

Journal of Organic Chemistry

Volumn 63, Issue 1, 1998, Pages 92-98

  Pihko, Petri M ^a   Koskinen, Ari M P ^a  

^a UNIVERSITY OF OULU   (Finland)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002500195     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo971167m     Document Type: Article

References (60)

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53. -1 and their isomeric composition with the oxazoles 4 and 20 (as evidenced by the HRMS data) are also indicative evidence for their structures. Equation presented.
54. 2/ HMTA/DBU oxidations also proceeded to completion within 2-3 h.
55. Our failure to prevent i and ii from forming despite our attempts to improve the N-silylation step could also be explained if they are formed as follows: intramolecular silyl transfer to the enolate anion (Brook rearrangement), cyclization of the resulting carbamate nitrogen-centered anion, and final loss of TMS from the ester. We thank the anonymous reviewer for pointing out this possibility.
56. The two methyl substituents are likely to considerably enhance the rate of cyclization and thus favor the formation of the side product. For an excellent discussion of this reactive rotamer effect, see: (a) Jung, M. E.; Gervay, J. J. Am. Chem. Soc. 1991, 113, 224-232. For recent studies of this effect with other than gem-dialkyl substituents, see: (b) De Corte, F.; Nuyttens, F.; Cauwberghs, S.; De Clercq, P. Tetrahedron Lett. 1993, 34, 1831-1832. (c) Agami, C.; Couty, F.; Hamon, L.; Venier, O. Tetrahedron Lett. 1993, 34, 4509-4512.
57. The two methyl substituents are likely to considerably enhance the rate of cyclization and thus favor the formation of the side product. For an excellent discussion of this reactive rotamer effect, see: (a) Jung, M. E.; Gervay, J. J. Am. Chem. Soc. 1991, 113, 224-232. For recent studies of this effect with other than gem-dialkyl substituents, see: (b) De Corte, F.; Nuyttens, F.; Cauwberghs, S.; De Clercq, P. Tetrahedron Lett. 1993, 34, 1831-1832. (c) Agami, C.; Couty, F.; Hamon, L.; Venier, O. Tetrahedron Lett. 1993, 34, 4509-4512.
58. The two methyl substituents are likely to considerably enhance the rate of cyclization and thus favor the formation of the side product. For an excellent discussion of this reactive rotamer effect, see: (a) Jung, M. E.; Gervay, J. J. Am. Chem. Soc. 1991, 113, 224-232. For recent studies of this effect with other than gem-dialkyl substituents, see: (b) De Corte, F.; Nuyttens, F.; Cauwberghs, S.; De Clercq, P. Tetrahedron Lett. 1993, 34, 1831-1832. (c) Agami, C.; Couty, F.; Hamon, L.; Venier, O. Tetrahedron Lett. 1993, 34, 4509-4512.
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