Observations on an iodocarbonate route to certain 1,3-diols related to the C22-34 subunit of FK-506

Journal of the Brazilian Chemical Society

Volumn 7, Issue 5, 1996, Pages 225-230

  Marshall, James A ^a   Xie, Shiping ^a  

^a UNIVERSITY OF VIRGINIA   (United States)

Author keywords

Allylic carbonate; Cyclic carbonate; Iodolactonization

Indexed keywords

EID: 0030501443     PISSN: 01035053     EISSN: None     Source Type: Journal    
DOI: 10.5935/0103-5053.19960047     Document Type: Article

References (10)

1. Marshall, J.A.; Xie, S. J. Org. Chem. 1995, 60, 7230.
2. Marshall, J.A.; Perkins, J. J. Org. Chem. 1994, 59, 3509.
3. Linde, R.G.; Egberson, M.; Coleman, R.S.; Jones A.B.; Danishefsky, S.J.J. Org. Chem. 1990, 55, 2771.
4. Corey, E.J.; Endus, D.; Bock, M.G. Tetrahedron Lett. 1976, 7.
5. Lindlar, H.; Dubuis, R. Organic Synthesis; Wiley: New York, 1973; collect. Vol V, p 880.
6. For previous studies on the use of IBr for related iodo carbonate cyclizations, see Duan, J. J-W.; Smith, A. B., III. J. Org. Chem. 1993, 58, 3703.
7. Rychnovsky, S.D.; Skalitzky, D.J. Tetrahedron Lett. 1990, 31, 945.
8. Marshall, J.A.; Hinkle, K.W. J. Org. Chem, 1995, 60, 1920.
9. Tirando, R.; Prieto, J.A. J. Org. Chem. 1993, 58, 5666.
10. 3. For typical experimental protocols, see Marshall, J.A.; Wang, X-J. J. Org. Chem. 1991, 56, 960.