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Total Synthesis of Leucascandrolide A

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Presentation on theme: "Total Synthesis of Leucascandrolide A"— Presentation transcript:

1 Total Synthesis of Leucascandrolide A
CHEM635 By: James L. Leighton Presented by: Kelsey Roberts

2 James L. Leighton 1987- BS from Yale University
Worked under Danishefsky Worked for Merck Research Labs. 1994- PhD from Harvard University Advisor was David A. Evans NSF Postdoc Under Eric N. Jacobsen at Harvard University Assistant professor at Columbia University Associate Professor 2004- Present- Full Professor at Columbia University

3 Leucascandrolide A Isolated from sponge Leucascandra caveolata in 1996
Strong in vitro cytotoxisity against KB and P388 cancer cells Potent antifungal 2 Oxygen bridged 18-membered macrolide.

4 Retrosynthesis

5 Retrosynthesis of 33

6 Scheme 1 (E)-crotyl-(-)-IPC2B

7 Scheme 1 (continued)

8 Scheme 1 (continued)

9 Scheme 2

10 Scheme 3

11 Scheme 4

12 Conclusion 20 Steps for the longest linear sequence Questions?

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