Synthesis of (-)-alantrypinone

Tetrahedron Letters

Volumn 40, Issue 30, 1999, Pages 5429-5432

  Hart, David J ^a   Magomedov, Nabi ^a  

^a OHIO STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALANTRYPINONE; BENZOXAZINE DERIVATIVE; NATURAL PRODUCT; QUINAZOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; ENANTIOMER; FUNGUS; PENICILLIUM; REACTION ANALYSIS; SYNTHESIS;

FUNGI; PENICILLIUM;

EID: 0033166696     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01005-9     Document Type: Article

References (18)

1. Larsen, T. O.; Frydenvang, K.; Frisvad, J. C.; Christophersen, C. J. Nat. Prod. 1998, 61, 1154.
2. Barrow, C. J.; Sun, H. H. J. Nat. Prod. 1994, 57, 471.
3. For our earlier studies directed toward spiroquinazoline see Hart, D. J.; Magomedov, N. J. Org. Chem. 1999, 64, 2990.
4. For other relevant studies and a different synthesis of 12 see He, F.; Snider, B. B. Synlett 1997, 483.
5. Nakagawa, M.; Taniguchi, M.; Sodeoka, M.; Ito, M.; Yamaguchi, K.; Hino, T. J. Am. Chem. Soc. 1983, 105, 3709.
6. This acid chloride was prepared from S-methyl cysteine using standard procedures as shown below: Carpino, L. A.; Cohen, B. J.; Stephens Jr., K. E.; Sadat-Aalaee, S. Y.; Tien, J.-H.; Langridge, D. C. J. Org. Chem. 1986, 51, 3732.
7. Mazurkiewicz, R. Monatsh. Chem. 1989, 120, 973.
8. Wang, H.; Ganesan, A. J. Org. Chem. 1998, 63, 2432.
9. He, F.; Snider, B. B. J. Org. Chem. 1999, 64, 1597. At the time this paper appeared we were aware, through our own studies to be reported at a later date, that the Ganesan report was in error.
10. Itoh, A.; Ozawa, S.; Oshima, K.; Nozaki, H. Tetrahedron Lett. 1980, 21, 361.
11. To our knowledge, this is the first example of Fmoc deprotection using this reagent.
12. 3 epimer of 10, stereochemistry being based on a chemical correlation with 12.
13. Rich, D. H.; Tam, J. P. J. Org. Chem. 1977, 42, 3815.
14. 2 (9.57 ppm).
15. For the conversion of indoles to oxindoles see Pellegrini, C.; Strassler, C.; Weber, M.; Borschberg, H.-J. Tetrahedron: Asymmetry 1994, 5, 1979. The conversion of 13 - 14+15 was shown to involve rapid formation of a mixture of diastereomeric bromoindolines followed by slower conversion to a mixture of 23-bromo-14, 23-bromo-15 and polybromination products. The mixture of crude bromoindoles was converted to 14 and 15 by hydrogenolysis over either platinum (faster) or palladium (slower) on carbon.
16. 1
17. 3 m/z 372.1222, found m/z 372.1276.
18. 1H NMR spectrum of this authentic sample was also identical to that recorded for 14.