Allyltitanates in stereospecific additions to chiral σ-lactol: Efficient enantioselective route to a potential precursor of the C1-C9 portion of Tylonolide

Journal of Organic Chemistry

Volumn 64, Issue 2, 1999, Pages 373-381

  Berque, Isabelle ^a   Le Ménez, Patrick ^a   Razon, Patrick ^a   Mahuteau, Jacqueline ^a   Férézou, Jean Pierre ^b   Pancrazi, Ange ^a   Ardisson, Janick ^a   Brion, Jean Daniel ^a  

^a UNIVERSITÉ PARIS SUD   (France)

^b LABORATOIRE DE SYNTHÈSE ORGANIQUE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; ALLYL COMPOUND; CARBAMIC ACID DERIVATIVE; DELTA LACTOL; SPARTEINE; TITANIUM DERIVATIVE; TYLONOLIDE; TYLOSIN; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; ENANTIOMER; STEREOCHEMISTRY; STEREOSPECIFICITY; STRUCTURE ANALYSIS;

EID: 0033593492     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9807722     Document Type: Article

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36. Le Ménez, P.; Fargeas, V.; Berque, I.; Poisson, J.; Ardisson, J.; Lallemand, J.-Y.; Pancrazi, A. J. Org. Chem. 1995, 60, 3592.
37. Our approch is slightly different from the synthesis of tylonolide developed by Marshall et al. (Marshall, J. A.; Yashunsky, D. V. J. Org. Chem. 1991, 56, 5493) which also involved a crucial step based on an allylation reaction.
38. Smith, N. D.; Kocienski, P. J.; Street, S. D. A. Synthesis 1996, 652. Férézou, J.-P.; Julia, M.; Li, Y.; Liu, L. W.; Pancrazi, A. Bull. Soc. Chim. Fr. 1995, 132, 428. Férézou, J.-P.; Julia, M.; Khourzom, R.; Li, Y.; Liu, L. W.; Pancrazi, A.; Robert, P. Synlett 1991, 611.
39. Smith, N. D.; Kocienski, P. J.; Street, S. D. A. Synthesis 1996, 652. Férézou, J.-P.; Julia, M.; Li, Y.; Liu, L. W.; Pancrazi, A. Bull. Soc. Chim. Fr. 1995, 132, 428. Férézou, J.-P.; Julia, M.; Khourzom, R.; Li, Y.; Liu, L. W.; Pancrazi, A.; Robert, P. Synlett 1991, 611.
40. Smith, N. D.; Kocienski, P. J.; Street, S. D. A. Synthesis 1996, 652. Férézou, J.-P.; Julia, M.; Li, Y.; Liu, L. W.; Pancrazi, A. Bull. Soc. Chim. Fr. 1995, 132, 428. Férézou, J.-P.; Julia, M.; Khourzom, R.; Li, Y.; Liu, L. W.; Pancrazi, A.; Robert, P. Synlett 1991, 611.
41. Second-order asymmetric induction was also described with the 1-(N,N-diisopropylcarbamoyloxy)-3-trimethylsilylallyl: Marsch, M.; Harms, K.; Zschage, O.; Hoppe, D.; Boche, G. Angew. Chem., Int. Ed. Engl 1991, 30, 321. When we tried to check this reaction with the 1-(N,N-diisopropylcarbamoyloxy)-4-dimethylphenylsilyl-2-butene(ref 8), no crystallization occurred and no enantioselective deprotonation could be obtained.
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49. For structural proof, compound 21 was converted into the bissilylated derivative 14.
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