Cationic bis(oxazoline)Cu(II) Lewis acid catalysts. Application to the asymmetric synthesis of ent-Δ1-tetrahydrocannabinol

Tetrahedron Letters

Volumn 38, Issue 18, 1997, Pages 3193-3194

  Evans, David A ^a   Shaughnessy, Eileen A ^a   Barnes, David M ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DRONABINOL;

ARTICLE; DRUG SYNTHESIS; ENANTIOMER; IN VITRO STUDY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030901232     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00609-6     Document Type: Article

References (18)

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4. Crombie, L.; Crombie, W. M. L.; Jamieson, S. V.; Palmer, C. J. J. Chem Soc., Perkin Trans. I 1988, 1243-1250.
5. (a) Evans, D. A.; Miller, S. J.; Lectka, T. J. Am. Chem. Soc. 1993, 115, 6460-6461.
6. (b) Evans, D. A.; Lectka, T.; Miller, S. J. Tetrahedron Lett. 1993, 34, 7027-7030.
7. (c)Evans, D. A.; Murry, J. A.; von Matt, P.; Norcross, R. D.; Miller, S. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 798-800.
8. (d) Evans, D. A.; Kozlowski, M. C.; Tedrow, J. S. Tetrahedron Lett. 1996, 37, 7481-7484.
9. (e) Evans, D. A.; Barnes, D. M. Tetrahedron Lett. 1997, 38, 57-58.
10. (a) Evans, D. A.; Murry, J. A.; Kozlowski, M. C. J. Am. Chem. Soc. 1996, 118, 5814-5815.
11. (b)Ref. 6d.
12. (a)Bailey, W. J.; Barclay, R. J. Org. Chem. 1955, 21, 328-331. Attempts to form the diene through the rearrangement of 2-methylbut-3-yn-2-ol with Ag(I) and acetic anhydride resulted in the formation of a mixture of products which were difficult to separate. See:
13. (b) Banks, R. E.; Miller, J. A.; Nunn, M. J.; Stanley, P.; Weakley, T. J.; Ullah, Z. J. Chem. Soc., Perkin Trans. I 1981, 1096-1102.
14. (c)Snider, B. B.; Amin S. G. Synth. Comm. 1978, 8, 117.
15. R (major) = 64 min, 79 min, (minor) = 31 min, 36 min).
16. Stoss, P.; Merrath, P. Synlett 1991, 553-554. Reaction at low concentration (0.003 M) minimized the formation of by-products.
17. (a) Petrzilka, T.; Haefliger, W.; Sikemeier, C. Helv. Chim. Acta 1969, 1102.
18. (b) Archer, R. A.; Johnson, D. W.; Hagaman, E. W.; Moreno, L. N.; Wenkert, E. J. Org. Chem. 1977, 42, 490-495.