Stereocontrolled Total Synthesis of (+)-Vinblastine Satoshi Yokoshima, Toshihiro Ueda, Satoshi Kobayashi, Ayato Sato, Takeshi Kuboyama, Hidetoshi Tokuyama,

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Stereocontrolled Total Synthesis of (+)-Vinblastine Satoshi Yokoshima, Toshihiro Ueda, Satoshi Kobayashi, Ayato Sato, Takeshi Kuboyama, Hidetoshi Tokuyama, and Tohru Fukuyama Presented By William Reid 2/26/13

(+)-Vinblastine Isolated from Catharanthus roseus Widely known agent for chemotherapy – Binds tubulin Only four previous syntheses

(+)-Vinblastine Isolated from Catharanthus roseus Widely known agent for chemotherapy – Binds tubulin Only four previous syntheses Required natural sources of (-)-vindoline

(+)-Vinblastine Isolated from Catharanthus roseus Widely known agent for chemotherapy – Binds tubulin Only four previous syntheses Required natural sources of (-)-vindoline Stereochemistry of C18

Goals Prepare an efficient route for the synthesis of (-)-vindoline – Improvement over biomimetic syntheses Control the stereocehemistry of C18 – Eleven membered ring intermediate Schill, G.; Priester, C. U.; Windho¨vel, U. F.; Fritz, H. Tetrahedron 1987, 43, 3765.

Retrosynthesis

Retrosynthesis 2 (-)-vindoline

Scheme 2 (-)-vindoline

Scheme 3

15

Scheme 3 Kobayashi, S.; Ueda, T.; Fukuyama, T. Synlett 2000, 883 (-)-vindoline

Scheme 4 (The Upper Half)

Scheme 5

Scheme 6 (+)-vinblastine

Conclusion Successfully synthesized (-)-vindoline Successfully synthesized 3 in 2% yield via a radical cyclization of o-alkenylthioanilide Successfully synthesized (+)-vinblastine – Correct stereochemistry – Convergence

Questions??