An asymmetric synthesis of (+)-apogossypol hexamethyl ether

Tetrahedron Letters

Volumn 37, Issue 6, 1996, Pages 791-792

  Meyers, A I ^a   Willemsen, Jeffrey J ^a  

^a Veterinary Dentistry and Oral Surgery   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

GOSSYPOL DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; ENANTIOMER; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030070786     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(95)02296-1     Document Type: Article

References (16)

1. Jaroszewski, J. W.; Strom-Hansen, T.; Hansen, L. L. Chirality 1992, 4, 216.
2. Fish, R. G.; Groundwater, P. W.; Morgan, G. J. J Tetrahedron: Asymmetry 1995, 6, 873, and references cited therein.
3. Matlin, S. A.; Belenguer, A.; Tyson, R. G.; Brookes, R. G. J. High Res.Chrom. 1987, 10, 86, and references cited therein.
4. Meltzer, P. C.; Bickford, P. H.; Lambert, G. H. J. Org. Chem. 1985, 50, 3121, and earlier synthetic approaches cited.
5. Meyers, A.I.; Gabel, R.; Mihelich, E.D. J. Org. Chem. 1978, 43, 1372.
6. Meyers, A.I.; Mihelich, E.D. J. Am. Chem. Soc. 1975, 97, 7383.
7. Barner, B. A.; Meyers, A.I. J. Am. Chem. Soc. 1984, 106, 1865.
8. Johnson, W. S.; Daub, G. H. Organic Reactions, 1951, 1.
9. For a typical carboxylic acid to oxazoline conversion see: Gant, T. G.; Meyers A. I. J. Am. Chem. Soc. 1992, 114, 1010.
10. Meyers, A.I.; Mihelich, E.D. J. Org. Chem. 1975, 40, 3158.
11. Nelson, T. D.; Meyers, A.I. J. Org. Chem. 1994, 59, 2655.
12. Nelson, T. D.; Meyers, A.I. Tetrahedron Lett. 1993, 34, 3061.
13. Chiralcel OD column, hexane,2-propanol (60:40), 1.0 mL/min.
14. It is noteworthy that enantiomerically pure apogossypol hexamethyl ether has not, to date, been described.
15. Moorlag, H; Meyers, A. I. Tetrahedron Lett. 1993, 34, 6993.
16. Nelson, T. D.; Meyers, A.I. J. Org. Chem. 1994, 59, 2655.