A new synthesis of (±)-mesembrine involving the intramolecular nucleophilic attack of an allyl anion on a carbonyl function of an imide

Tetrahedron Letters

Volumn 38, Issue 11, 1997, Pages 1893-1894

  Rajagopalan, P ^a  

^a DUPONT COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; MESEMBRINE; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS;

EID: 0031575741     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00202-5     Document Type: Article

References (9)

1. 1. Kamireddy, B.; Magolda, R.L.; Reddy, G.S. Private communication. These authors used benzyl tri-n-butylammonium fluoride in their cyclizations. Thanks are due to Dr. Kamireddy for details pertaining to this reaction.
2. Popelak, A.; Lettenbauer, G.The Alkaloids, Manske, R.H.F. Ed.; Academic Press; New York, NY, 1967; Vol. IX; Chap. 11. Lewis, J.R. Nat. Prod. Rept., 1994, 11, 329.
3. Popelak, A.; Lettenbauer, G.The Alkaloids, Manske, R.H.F. Ed.; Academic Press; New York, NY, 1967; Vol. IX; Chap. 11. Lewis, J.R. Nat. Prod. Rept., 1994, 11, 329.
4. 3. Gramain, J.-C; and Remuson, R. Tetrahedron Lett. 1985, 26, 4083. Taguchi, H.; Oh-Ishi, T.; Kugita, H. Chem. Pharm. Bull., 1970, 18, 299.
5. 3. Gramain, J.-C; and Remuson, R. Tetrahedron Lett. 1985, 26, 4083. Taguchi, H.; Oh-Ishi, T.; Kugita, H. Chem. Pharm. Bull., 1970, 18, 299.
6. 4. The NMR and mass spectra of this compound were consistent with the structural assignment.
7. 5. This part was presented at the 18th IUPAC Symposium on Natural Products, Strasbourg, France, September, 1992.
8. 6. Many syntheses of racemic, (+)-and (-)-mesembrine are known. For pertinent references, cf. Nemoto, H.; Tanabe, T.; Fukumoto, K. J. Org. Chem., 1995, 60, 6785.
9. 7. Stevens, R.V.; Wentland, M.P. J. Amer. Chem. Soc., 1968, 90, 5580.