Asymmetric synthesis of the core structure of the melodinus alkaloids

Tetrahedron Letters

Volumn 40, Issue 4, 1999, Pages 645-648

  Schultz, Arthur G ^a   Dai, Mingshi ^a  

^a Research Rensselaer Polytechnic Institute   (United States)

Author keywords

Alkaloids; Asymmetric synthesis; Enolates; Mannich reactions

Indexed keywords

ALKALOID; LACTONE DERIVATIVE; MELOSCINE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CHEMICAL STRUCTURE; PROTON NUCLEAR MAGNETIC RESONANCE; REDUCTION; SYNTHESIS;

MELODINUS;

EID: 0033593302     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)02510-6     Document Type: Article

References (12)

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5. For the most recent application of the asymmetric Birch reduction-alkylation in the synthesis of natural products, see: Schultz, A. G.; Wang, A. J. Am. Chem. Soc. 1998, 120, 8259-8260.
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7. The diastereomeric purity of 4 was determined to be >20:1 by HPLC comparison to a 1:1 mixture of diastereomers prepared from the racemic carboxylic acid corresponding to 3.
8. 3. (Formula Presented)
9. 3SnH, see: Chang, H. S.; Bergmeier, S. C; Frick, J. A.; Bathe, A.; Rapoport, H. J. Org. Chem. 1994, 59, 5336-5342.
10. + + 1, 100).
11. For a recent review of the Mannich reaction, see: Arend, M.; Westermann, B.; Risch, N. Angew. Chem. Intl. Ed. Engl. 1998, 37, 1044-1070.
12. Schultz, A. G.; Green, N. J. J. Am. Chem. Soc. 1992. 114, 1824-1829.