Studies of new indole alkaloid coupling methods for the synthesis of haplophytine

Organic Letters

Volumn 8, Issue 14, 2006, Pages 3117-3120

  Rege, Pankaj D ^a   Tian, Yuan ^a   Corey, E J ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

INDOLE ALKALOID; PHYTIC ACID CALCIUM MAGNESIUM SALT;

APOCYNACEAE; ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; MEDICINAL PLANT; NUCLEAR MAGNETIC RESONANCE; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

APOCYNACEAE; CRYSTALLOGRAPHY, X-RAY; INDOLE ALKALOIDS; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; PLANTS, MEDICINAL;

EID: 33746614029     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol061319c     Document Type: Article

References (18)

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13. 3CCO to the lactam carbonyl oxygen as well as to the imine nitrogen.
14. 2O did afford the coupling product with 13 but only in lower yield.
15. See the Supporting Information for details.
16. The peak assignment is based on comparison with similar compounds and their splitting pattern.
17. It was found that protic acids seem to work best for this type of reaction. Use of Lewis acid did not lead to high desired product formation. The major product in these cases was the diol.
18. On the basis of comparison with closely related natural product cimilophytine. See: Adesomoju, A. A.; Rawal, V. H.; Lakshmikantham, M. V.; Cava, M. P. J. Org. Chem. 1983, 48, 3015.