Novel rearrangement of a 2-aryl-3-alkyl-3H-indol-3-ol to a 1,4,5,6-tetrahydro-2,6-methano-1-benzazocin-3(2H)-one with implications for the biosynthesis of aspernomine

Organic Letters

Volumn 5, Issue 3, 2003, Pages 333-335

  Liu, Yahua ^a   McWhorter Jr , William W ^a   Hadden, Chad E ^a  

^a PFIZER INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1,4,5,6 TETRAHYDRO 2,6 METHANO 1 BENZAZOCIN 3(2H) ONE; 2 (2 BROMOPHENYL) 3 (3 BUTENYL) 3H INDOL 3 OL; ASPERNOMINE; BENZAZOCINE DERIVATIVE; DITERPENOID; INDOLE DERIVATIVE; UNCLASSIFIED DRUG; DITERPENE; FUSED HETEROCYCLIC RINGS; NOMININE;

ARTICLE; CHEMICAL REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; REACTION ANALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; METABOLISM; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS;

DITERPENES; HETEROCYCLIC COMPOUNDS WITH 4 OR MORE RINGS; HETEROCYCLIC COMPOUNDS, 3-RING; INDOLES; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE;

EID: 0038518310     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0202417     Document Type: Article

References (8)

1. Gloer, J. B.; Rinderknecht, B. T.; Wicklow, D. T.; Dowd, P. F. J. Org. Chem. 1989, 54, 2530.
2. Staub, G. M.; Gloer, J. B.; Wicklow, D. T.; Dowd, P. F. J. Am. Chem. Soc. 1992, 114, 1015.
3. (a) Blackman, A. J.; Hambly, T. W.; Picker, K.; Taylor, W. C.; Thirasasana, N. Tetrahedron Lett. 1987, 28, 5561.
4. (b) Liu, Y.; McWhorter, W. W. J. Am. Chem. Soc. Accepted for publication.
5. Prepared by the procedure in: Richman, R. J.; Hassner, A. J. Org. Chem. 1968, 33, 2548.
6. Dalton, L.; Humphrey, G. L.; Cooper, M. M.; Joule, J. A. J. Chem. Soc., Perkin Trans. 1 1983, 2417.
7. 16-BrNO: C, 63.17; H, 4.71; N, 4.09. Found: C, 63.04; H, 4.78; N, 4.00. mp 217.0-219.5°C.
8. See: Nakagawa, M.; Matsuki, K.; Hasegawa, K.; Hino, T. J. Chem. Sot., Chem. Commun. 1982, 742 and references therein.