An asymmetric synthesis of the ant venom alkaloid (3S,5S,8aR)-3-butyl-5-(4-pentenyl)indolizidine via the sharpless asymmetric dihydroxylation

Heterocycles

Volumn 42, Issue 1, 1996, Pages 39-42

  Takahata, Hiroki ^a   Bandoh, Hiroshi ^a   Momose, Takefumi ^a  

^a UNIVERSITY OF TOYAMA   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0003118186     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-95-S8     Document Type: Article

References (14)

1. H. Takahata and T. Momose, In The Alkaloids; G. A. Cordell, Ed., Academic Press: San Diego, 1993; Vol 44, pp. 189-256.
2. T. H. Jones, A. Laddago, A. W. Don, and M. S. Blum, J. Nat. Prod., 1990, 53, 375.
3. a) H. C. Kolb, M. S. VanNieuwehze, and K. B. Sharpless, Chemical Reviews, 1994, 94, 2483;
4. b) R. A. Johnson, and K. B. Sharpless, In Catalytic Asymmetric Synhess; I. Ojima, Ed., VCH Publishers Inc.: New York, 1993; pp. 227-272.
5. S. C. Sinha and E. Keinan, J. Am. Chem. Soc., 1993, 115, 4891;
6. b) Idem, J. Org. Chem., 1994, 59, 949.
7. a) H. Takahata, K. Inose, and T. Momose, Heterocycles, 1994, 38, 269;
8. b) H. Takahata, K. Inose, N. Araya, and T. Momose, Heterocycles, 1994, 38, 1961.
9. a) H. Takahata, H. Takehara, N. Ohkubo, and T. Momose, Tetrahedron:Asymmetry, 1990, 1, 561;
10. b) H. Takahata, H. Bandoh, and T. Momose, J. Org. Chem., 1992, 57, 4401;
11. c) Idem, Heterocycles, 1993, 36, 2777.
12. A. Basha, M. Lipton, and S. M. Weinreb, Tetrahedron Lett., 1977, 4171.
13. 3) δ14.11, 19.32, 20.04, 23.10, 26.93, 27.73, 28.31, 28.77, 29.46, 32.43, 32.54, 34.07, 52.64, 56.27, 58.54, 114.44, 138.92.
14. The optical rotation of natural product (1) is not reported in ref.2.