Geminal Acylation with Methyl-Substituted Analogues of 1,2-Bis[(trimethylsilyl)oxy]cyclobutene

Journal of Organic Chemistry

Volumn 62, Issue 25, 1997, Pages 8722-8729

  Crane, Sheldon N ^a   Jenkins, Tracy J ^a   Jean Burnell, D ^a  

^a MEMORIAL UNIVERSITY OF NEWFOUNDLAND   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

CHLOROTHRICOLIDE; KIJANOLIDE; NAPHTHALENE DERIVATIVE; TETROCARCIN; TETRONOLIDE; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ARTICLE; DRUG SYNTHESIS; ENANTIOMER; MOLECULAR INTERACTION; NONHUMAN; REACTION ANALYSIS; SARCOMA; STRUCTURE ANALYSIS;

EID: 0031454353     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo971055v     Document Type: Article

References (31)

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20. Other developments and synthetic uses of Lewis acid-catalyzed geminal acylation with 1: (a) Anderson, W. K.; Lee, G. E. Synth. Commun. 1980, 10, 351-354. (b) Nakamura, E.; Shimada, J; Kuwajima, I. J. Chem. Soc., Chem. Commun. 1983, 498-499. (c) Bunnelle, W. H.; Shangraw, W. R. Tetrahedron 1987, 43, 2005-2011. (d) Martinez, R. A.; Rao, P. N.; Kim, H. K. Synth. Commun. 1989, 19, 373-377. (e) Pandey, B.; Khire, U. R.; Ayyangar, N. R. Synth. Commun. 1989, 19, 2741-2747. (f) Liu, P.-Y.; Burnell, D. J. J. Chem. Soc., Chem. Commun. 1994, 1183-1184. (g) Liu, P.-Y.; Wu, Y.-J.; Burnell, D. J. Can. J. Chem. 1997, 75, 656-664.
21. Other developments and synthetic uses of Lewis acid-catalyzed geminal acylation with 1: (a) Anderson, W. K.; Lee, G. E. Synth. Commun. 1980, 10, 351-354. (b) Nakamura, E.; Shimada, J; Kuwajima, I. J. Chem. Soc., Chem. Commun. 1983, 498-499. (c) Bunnelle, W. H.; Shangraw, W. R. Tetrahedron 1987, 43, 2005-2011. (d) Martinez, R. A.; Rao, P. N.; Kim, H. K. Synth. Commun. 1989, 19, 373-377. (e) Pandey, B.; Khire, U. R.; Ayyangar, N. R. Synth. Commun. 1989, 19, 2741-2747. (f) Liu, P.-Y.; Burnell, D. J. J. Chem. Soc., Chem. Commun. 1994, 1183-1184. (g) Liu, P.-Y.; Wu, Y.-J.; Burnell, D. J. Can. J. Chem. 1997, 75, 656-664.
22. Other developments and synthetic uses of Lewis acid-catalyzed geminal acylation with 1: (a) Anderson, W. K.; Lee, G. E. Synth. Commun. 1980, 10, 351-354. (b) Nakamura, E.; Shimada, J; Kuwajima, I. J. Chem. Soc., Chem. Commun. 1983, 498-499. (c) Bunnelle, W. H.; Shangraw, W. R. Tetrahedron 1987, 43, 2005-2011. (d) Martinez, R. A.; Rao, P. N.; Kim, H. K. Synth. Commun. 1989, 19, 373-377. (e) Pandey, B.; Khire, U. R.; Ayyangar, N. R. Synth. Commun. 1989, 19, 2741-2747. (f) Liu, P.-Y.; Burnell, D. J. J. Chem. Soc., Chem. Commun. 1994, 1183-1184. (g) Liu, P.-Y.; Wu, Y.-J.; Burnell, D. J. Can. J. Chem. 1997, 75, 656-664.
23. Other developments and synthetic uses of Lewis acid-catalyzed geminal acylation with 1: (a) Anderson, W. K.; Lee, G. E. Synth. Commun. 1980, 10, 351-354. (b) Nakamura, E.; Shimada, J; Kuwajima, I. J. Chem. Soc., Chem. Commun. 1983, 498-499. (c) Bunnelle, W. H.; Shangraw, W. R. Tetrahedron 1987, 43, 2005-2011. (d) Martinez, R. A.; Rao, P. N.; Kim, H. K. Synth. Commun. 1989, 19, 373-377. (e) Pandey, B.; Khire, U. R.; Ayyangar, N. R. Synth. Commun. 1989, 19, 2741-2747. (f) Liu, P.-Y.; Burnell, D. J. J. Chem. Soc., Chem. Commun. 1994, 1183-1184. (g) Liu, P.-Y.; Wu, Y.-J.; Burnell, D. J. Can. J. Chem. 1997, 75, 656-664.
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27. Rühlmann, K. Synthesis 1971, 236-253.
28. With the norbornyl system, exo addition of 3 was very likely favored with both the ketone and its acetal, but, as can be seen in entry 5, this system showed the largest, yet obviously different, stereoselectivities with ketone and acetal.
29. Dewar, M. J. S.; Zoebisch, E. G.; Healy, K. F.; Stewart, J. J. P. J. Am. Chem. Soc. 1985, 107, 3902-3909 using SPARTAN, Version 4.1 (Wavefunction, Inc., Irvine, CA).
30. 3 gave a 1.2:1 mixture of 36a and its epimer 36c in a total yield of 36%. As this process showed essentially no stereoselectivity, reactions of acetals with 4 were not pursued further.
31. Atomic coordinates for the X-ray structures of 11c, 33c, 36b, 46a, and 48 have been deposited with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK.