Approaches to diene based homopumiliotoxin alkaloids

Tetrahedron Letters

Volumn 37, Issue 39, 1996, Pages 7151-7154

  McAlonan, Helena ^a   Montgomery, David ^a   Stevenson, Paul J ^a  

^a QUEEN'S UNIVERSITY BELFAST   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; PUMILIOTOXIN;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030599230     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01564-X     Document Type: Article

References (20)

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13. 7. Van Horn, D.E.; Negish E. J. Amer. Chem. Soc. 1978, 100, 2252-2254. Arcadi, A.; Bernocchi, E.; Barini, A.; Cacchi, S.; Marinell, F.; Pietroni, B. Tetrahedron Lett. 1989, 30, 3465-3468. For a review reactions of acetylenes with vinyl bromides see Negishi, E.; Coperet, C.; Ma, S. Lious, S. Liu, F. Chem. Rev. 1996, 96, 365-393.
14. 7. Van Horn, D.E.; Negish E. J. Amer. Chem. Soc. 1978, 100, 2252-2254. Arcadi, A.; Bernocchi, E.; Barini, A.; Cacchi, S.; Marinell, F.; Pietroni, B. Tetrahedron Lett. 1989, 30, 3465-3468. For a review reactions of acetylenes with vinyl bromides see Negishi, E.; Coperet, C.; Ma, S. Lious, S. Liu, F. Chem. Rev. 1996, 96, 365-393.
15. 8. Burns, B.; Grigg, R.; Sridharan, V.; Worakun, T. Tetrahedron Lett. 1988, 29, 4325-4328.
16. 9. These alkylation conditions are known to cause partial epimerisation in closely related systems. The optical purity of product (2a) was not checked but it can be safely assumed that it is not optically pure. If optically pure material is required then this can be achieved by alkylation of diethylglutamate followed by cyclisation see McAlonan, H.; Stevenson, P. Tetrahedron Asymmetry 1995, 6, 239-244.
17. 10. Corey, E.J.; Fuchs, P.L. Tetrahedron Lett. 1972, 3769-3772. Reetz, M.T.; Strack, T.J.; Kanand, J. Goddard, R. J. Chem. Soc. Chem. Comm. 1996, 733-734.
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19. 11. S-2-Aminoadipic acid although commercially available is very expensive. For a preparation see Moloney, M.G. Tetrahedron Asymmetry 1994, 1463-1464. Bailey has recently reported an elegant synthesis of a diazoketone which on Wolff rearrangement should give S-2-aminoadipic acid. See Adams, D.R.; Bailey, P.D.; Collier, I.D.; Heffernan, J.D.; Stokes, S. J. Chem. Soc. Chem. Comm. 1996, 349-350.
20. 11. S-2-Aminoadipic acid although commercially available is very expensive. For a preparation see Moloney, M.G. Tetrahedron Asymmetry 1994, 1463-1464. Bailey has recently reported an elegant synthesis of a diazoketone which on Wolff rearrangement should give S-2-aminoadipic acid. See Adams, D.R.; Bailey, P.D.; Collier, I.D.; Heffernan, J.D.; Stokes, S. J. Chem. Soc. Chem. Comm. 1996, 349-350.