A new synthesis of (-)-mesembrine employing sharpless AD reaction and new radical-initiated reaction

Heterocycles

Volumn 42, Issue 1, 1996, Pages 135-139

  Yoshimitsu, Takehiko ^a   Ogasawara, Kunio ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001065572     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-95-s46     Document Type: Article

References (15)

1. A pertinent review, see: H. C. Kolb, M. S. VanNieuwenhze, and K. B. Sharpless, Chem. Rev., 1994, 94, 2483.
2. S. Takano, T. Yoshimitsu, and K. Ogasawara, J. Org. Chem., 1994, 59, 54. See also: Z. -M. Wang, K. Kakiuchi, and K. B. Sharpless, J. Org. Chem., 1994, 59, 6895.
3. S. Takano, T. Yoshimitsu, and K. Ogasawara, J. Org. Chem., 1994, 59, 54. See also: Z. -M. Wang, K. Kakiuchi, and K. B. Sharpless, J. Org. Chem., 1994, 59, 6895.
4. Our previous attemption based on conceptionally the same methodology employing the enantiospecific iodo-lactonization reaction, see: S. Takano, C. Murakata, Y. Imamura, N. Tamura, and K. Ogasawara, Heterocycles, 1981, 16, 1291; S. Takano, C. Kasahara, and K. Ogasawara, ibid., 1982, 19, 1443.
5. Our previous attemption based on conceptionally the same methodology employing the enantiospecific iodo-lactonization reaction, see: S. Takano, C. Murakata, Y. Imamura, N. Tamura, and K. Ogasawara, Heterocycles, 1981, 16, 1291; S. Takano, C. Kasahara, and K. Ogasawara, ibid., 1982, 19, 1443.
6. A pertinent review of the Sceletium and the related alkaloids: J. R. Lewis, Nat. Prod. Rept., 1994, 11, 329 and the preceding reviews.
7. S. Takano, Y. Imamura, and K. Ogasawara, Chem. Lett., 1981, 1385.
8. For brevity the stereochemistry of the quaternary center was indicated.
9. Purchased from Aldrich and used without further purification.
10. 4Cl in aqueous EtOH gave no trace of 15.
11. A little related radical fragmentation reaction: a) J. Y. Godet and M. Pereye, Bull. Soc. Chim. Fr., 1976, 1105. b) G. L. Lange and C. Gottardo, Tetrahedron Lett., 1990, 31, 5985.
12. A little related radical fragmentation reaction: a) J. Y. Godet and M. Pereye, Bull. Soc. Chim. Fr., 1976, 1105. b) G. L. Lange and C. Gottardo, Tetrahedron Lett., 1990, 31, 5985.
13. Identical with an authentic material prepared by an enantioselective route see: S. Takano, Y. Imamura, and K. Ogasawara, Tetrahedron Lett., 1981, 22, 4479;
14. S. Takano, K. Samizu, and K. Ogasawara, Chem. Lett., 1990, 1239.
15. Optical purity was determined at the enone (16) by hplc using a chiral column (CHIRALCEL OD: eluent 15% i-PrOH-hexane).