Total synthesis of (-)-funebrine via Au-catalyzed regio- and stereoselective γ-butyrolactonization of allenylsilane

Tetrahedron Letters

Volumn 52, Issue 44, 2011, Pages 5744-5746

  Okada, Takuya ^a   Sakaguchi, Kazuhiko ^a   Shinada, Tetsuro ^a   Ohfune, Yasufumi ^a  

^a Osaka Prefecture University   (Japan)

Author keywords

( ) Funebrine; Allenylsilane; Au catalyzed lactonization; Paal Knorr pyrrole condensation; Butyrolactone

Indexed keywords

1,4 DIKETONE; ALLENYLSILANE; ALPHA ACYLOXY ALPHA ALKYNYLSILANE; FUNEBRINE; GOLD; NATURAL PRODUCT; PYRROLE; SILANE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CLAISEN REARRANGEMENT; GAMMA BUTYROLACTONIZATION; LACTONIZATION; SYNTHESIS;

EID: 80055003096     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.08.050     Document Type: Article

References (12)

1. Raffauf, R. F.; Zennie, T. M.; Onan, K. D.; Le Quesne, P. W. J. Org. Chem. 1984, 49, 2714-2718.
2. (a) Tamura, O.; Iyama, N.; Ishibashi, H. J. Org. Chem. 2004, 69, 1475-1480;
3. (b) Racemic synthesis: Dong, Y.; Pai, N. N.; Ablaza, S. L.; Yu, S.-X.; Bolvig, S.; Forsyth, D. A.; Le Quesne, P. W. J. Org. Chem. 1999, 64, 2657-2666.
4. Okada, T.; Oda, N.; Suzuki, H.; Sakaguchi, K.; Ohfune, Y. Tetrahedron Lett. 2010, 51, 3765-3768.
5. Matsuo, J.; Iida, D.; Yamanaka, H.; Mukaiyama, T. Tetrahedron 2003, 59, 6739-6750.
6. (a) Soderquist, J. A.; Anderson, C. L.; Miranda, E. I.; Rivera, I. Tetrahedron Lett. 1990, 31, 4677-4680;
7. (b) Dahr, R. K. Aldrichim. Acta 1994, 27, 43-51.
8. (a) Corey, E. J.; Bakshi, R. K.; Shibata, S. J. Am. Chem. Soc. 1987, 109, 5551-5553;
9. (b) Deloux, L.; Srebnik, M. Chem. Rev. 1993, 93, 763-784;
10. (c) Parker, K. A.; Ledeboer, M. W. J. Org. Chem. 1996, 61, 3214-3217.
11. Lichtenthaler, F. W.; Brust, A.; Cuny, E. Green Chem. 2001, 3, 201-209.
12. Using EtOH instead of 2-PrOH as the solvent during the removal of the THP group, the ethyl ether of 2 was obtained in 66% yield (Scheme 6).