Concise total synthesis of (±)-palominol and (±)-dolabellatrienone via a dianion-accelerated oxy-Cope rearrangement

Tetrahedron Letters

Volumn 39, Issue 8, 1998, Pages 741-744

  Corey, E J ^a   Kania, Robert S ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DITERPENOID; DOLABELLATRIENONE; FARNESOL; PALOMINOL; UNCLASSIFIED DRUG;

ARTICLE; BACTERICIDAL ACTIVITY; CONTROLLED STUDY; CYCLIZATION; DRUG SYNTHESIS; NONHUMAN; WARMING;

EID: 0032546076     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10614-1     Document Type: Article

References (36)

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30. 13C NMR, IR and MS obtained for synthetic 1 were identical to those recorded previously. For data, see: Caceres, J.; Rivera, M. E.; Rodriguez, A. D. Tetrahedron 1990, 46, 3422. For corrected structure, see: Shin, J.; Fenical, W. J. Org. Chem. 1991, 56, 3392.
31. 13C NMR, IR and MS obtained for synthetic 1 were identical to those recorded previously. For data, see: Caceres, J.; Rivera, M. E.; Rodriguez, A. D. Tetrahedron 1990, 46, 3422. For corrected structure, see: Shin, J.; Fenical, W. J. Org. Chem. 1991, 56, 3392.
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34. 13C NMR, UV, IR and MS data obtained for synthetic 2 were identical with those obtained for natural dolabellatrienone. We are grateful to Dr. William Fenical for providing copies of the spectra of natural 2.
35. 13. The X-ray crystal diffraction analysis was performed by Dr. Mark C. Noe. Detailed X-ray crystallographic data are available from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK.
36. 14. This research was generously supported by the National Science Foundation and the National Institutes of Health.