A formal total synthesis of (-)-cephalotaxine.

M IKEDA, SAA El Bialy, K HIROSE, M Kotake…

Index: Ikeda, Masazumi; Serry; Bialy, El; Hirose, Ken-Ichi; Kotake, Miho; Sato, Tatsunori; Bayomi, Said M. M.; Shehata, Ihsan A.; Abdelal, Ali M.; Gad, Laila M.; Yakura, Takayuki Chemical and Pharmaceutical Bulletin, 1999 , vol. 47, # 7 p. 983 - 987

Full Text: HTML

Citation Number: 27

Abstract

A formal total synthesis of (-)-cephalotaxine (1) has been achieved. The key step is an intramolecular aldol condensation of the diketone 9, which in turn was obtained in three steps from the azabicyclic compound 6 derived from D-proline according to Seebach's procedure. Treatment of 9 with a catalytic amount of sodium 2-methyl-2-butanolate in benzone at room temperature gave the α, β-unsaturated ketone 8 in 43% yield. Catalytic ...

Related Articles:

Ester-enolate Claisen rearrangement of proline-containing α-acyloxy-α-vinylsilane. Synthesis of pyrrolidine-fused glutamate analogs

[Sakaguchi, Kazuhiko; Yamamoto, Masahiro; Watanabe, Yusuke; Ohfune, Yasufumi Tetrahedron Letters, 2007 , vol. 48, # 28 p. 4821 - 4824]

Ester-enolate Claisen rearrangement of proline-containing α-acyloxy-α-vinylsilane. Synthesis of pyrrolidine-fused glutamate analogs

[Sakaguchi, Kazuhiko; Yamamoto, Masahiro; Watanabe, Yusuke; Ohfune, Yasufumi Tetrahedron Letters, 2007 , vol. 48, # 28 p. 4821 - 4824]

More Articles...