The Florisil® catalyzed [1,3]-sigmatropic shift of allyl phenyl ethers - An entryway into novel mycophenolic acid analogues

Tetrahedron Letters

Volumn 38, Issue 27, 1997, Pages 4725-4728

  Talamás, Francisco X ^a   Smith, David B ^a   Cervantes, Alicia ^b   Franco, Fidencio ^b   Cutler, Serena T ^b   Loughhead, David G ^b   Morgans Jr , David J ^b   Weikert, Robert J ^b  

^a ROCHE BIOSCIENCE   (United States)

^b NONE

Author keywords

[No Author keywords available]

Indexed keywords

MAGNESIUM TRISILICATE; MYCOPHENOLIC ACID;

ARTICLE; CATALYSIS; CHEMICAL MODIFICATION; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0030913075     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00949-0     Document Type: Article

References (8)

1. Dauben, W. G.; Cogen, J. M.; Behar, V. Tetrahedron Lett. 1990, 31, 3241.
2. For an application of the Dauben procedure in the context of a total synthesis, see: Corey, E. J.; Wu, L. I. J. Am. Chem. Soc. 1993, 115, 9327.
3. (a) Nelson, P. H.; Eugui, E.; Wang, C. C.; Allison, A. C. J. Med. Chem. 1990, 33, 833.
4. (b) Smith, D. B.; Waltos, A. M.; Loughhead, D. G.; Weikert, R. J.; Morgans, D. J. Jr.; Rohloff, J. C.; Link, J. O.; Zhu, R. J. Org. Chem. 1996, 61, 2236.
5. 6 For alternate syntheses of 2, see: a) Patterson, J. W. Tetrahedron 1993, 49, 4789.
6. b) Watanabe, M.; Tsukazaki, M.; Hamada, Y.; Iwao, M.; Furukawa, S. Chem. Pharm. Bull. 1989, 37, 2948.
7. For information and references related to the preparation of the deuterated substrates 3a and 3b, and their use in a related investigation, see: Smith, D. B.; Elworthy, T. R.; Morgans, D. J. Jr.; Nelson, J. T.; Patterson, J. W.; Vasquez, A.; Waltos, A. M. Tetrahedron Lett. 1996, 37, 21.
8. Smith, D. B.; Talamas, F. X.; Morgans, D. J. Jr., manuscripts in preparation.