Total synthesis and absolute configuration of (-)-gummiferol

Organic Letters

Volumn 13, Issue 14, 2011, Pages 3644-3647

  Takamura, Hiroyoshi ^a   Wada, Hiroko ^a   Lu, Nan ^a   Kadota, Isao ^a  

^a OKAYAMA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID DERIVATIVE; BIOLOGICAL PRODUCT; FATTY ALCOHOL; GUMMIFEROL;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; NUCLEAR MAGNETIC RESONANCE; STEREOISOMERISM; SYNTHESIS;

ACETATES; BIOLOGICAL PRODUCTS; FATTY ALCOHOLS; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; STEREOISOMERISM;

EID: 79960175078     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol201301b     Document Type: Article

References (14)

1. Fullas, F.; Brown, D. M.; Wani, M. C.; Wall, M. E.; Chagwedera, T. E.; Farnsworth, N. R.; Pezzuto, J. M.; Kinghorn, A. D. J. Nat. Prod. 1995, 58, 1625
2. Katsuki, T.; Sharpless, K. B. J. Am. Chem. Soc. 1980, 102, 5974
3. Brandsma, L. Preparative Acetylenic Chemistry, 2 nd ed.; Elsevier: Amsterdam, 1988.
4. Siemsen, P.; Livingston, R. C.; Diederich, F. Angew. Chem., Int. Ed. 2000, 39, 2632
5. Zhang, P.; Morken, J. P. J. Am. Chem. Soc. 2009, 131, 12550
6. Ohtani, I.; Kusumi, T.; Kashman, Y.; Kakisawa, H. J. Am. Chem. Soc. 1991, 113, 4092
7. Finan, J. M.; Kishi, Y. Tetrahedron Lett. 1982, 23, 2719
8. Parikh, J. R.; Doering, W. v. E. J. Am. Chem. Soc. 1967, 89, 5505
9. Blanchette, M. A.; Choy, W.; Davis, J. T.; Essenfeld, A. P.; Masamune, S.; Roush, W. R.; Sakai, T. Tetrahedron Lett. 1984, 25, 2183
10. Corey, E. J.; Fuchs, P. L. Tetrahedron Lett. 1972, 3769
11. 3N, only a trace amount of 15 was obtained because the epoxide opening occurred as a side reaction. For the related examples, see: Grandjean, D.; Pale, P.; Chuche, J. Tetrahedron Lett. 1994, 35, 3529
12. González, I. C.; Forsyth, C. J. J. Am. Chem. Soc. 2000, 122, 9099
13. Díaz, D.; Martín, T.; Martín, V. S. J. Org. Chem. 2001, 66, 7231
14. Reber, S.; Knöpfel, T. F.; Carreira, E. M. Tetrahedron 2003, 59, 6813