Total synthesis of the axane-4 family of sesquiterpenoids using a stereoselective intramolecular conjugate addition

Synlett

Volumn 1989, Issue 1, 1989, Pages 49-51

  Hart, David J ^a   Lai, Chin Shan ^a  

^a OHIO STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 85023313060     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-1989-34696     Document Type: Article

References (12)

1. Cafieri, F.; Fatturoso, E.; Magno, S.; Santacroce, Sica, A. Tetrahedron 1973, 29, 4259.
2. Fatturoso, E.; Magno, S.; Mayol, L.; Santacroce, C; Sica, D. Tetrahedron 1975, 31, 269.
3. Iengo, A.; Mayol, L.; Santacroce, C. Experentia 1977, 33, 11.
4. Omino, G.; DeRosa, S.; DeStefano, S.; Sodano, G. Comp. Biochem. Physiol. 1982, 73 B, 471.
5. Adinolfi, M.; DeNapoli, L.; DiBlasio, B.; Iengo, A.; Pedone, C; Santacroce, C. Tetrahedron Lett. 1977, 2185.
6. Piers, E.; Yeung, B. W. A.; Rettig, S. J. Tetrahedron 1987, 43, 5521. This paper resolves some structural ambiguities that appear in reference 5.
7. Piers, E.; Yeung, B. W. A. Can. J. Chem. 1986, 64, 2475.
8. Brattesani, D. N.; Heathcock, C. H. J. Org. Chem. 1975, 40, 2165.
9. House, H. O.; Gannon, W. F. Org. Synth Coll Vol. V 1973, 539.
10. Ester 14 was prepared in 48% yield using a Ni (0)-mediated coupling of the lithium enolate of tor-butyl (trimethylsilyl) - acetate with 2-bromopropene. See: Albaugh-Robertson, P.; Katzenellenbogen, J. A. J. Org. Chem. 1983, 48, 5288.
11. Millard, A. A.; Rathke, M. W. J. Am. Chem. Soc 1977, 99, 4833.
12. Shioiri, T.; Yamada, S. Chem. Pharm. Butt. 1974, 22, 849.