1. Total Synthesis of the Antimitotic Bicyclic Peptide Celogentin C
Bing Ma, Biplab Banerjee, Dmitry N. Litvinov, Liwen He, and Steven L. Castle J. Am. Chem. Soc. 2010, 132,
Corey Basch
Synthesis Presentation
3/19/13

2. Steven L. Castle CV
: Summer research assistant, U. of South Florida, (4).
advisor: Raymond N. Castle
: B.S. Chemistry, Brigham Young University, (1).
advisor: Jerald S. Bradshaw
: PhD Chemistry, Scripps Research Institute, (12).
advisor: Dale. L. Boger
: Assistant Professor, Dept. Chemistry and Biochemistry, Brigham Young University, (26).
2008-Present: Associate Professor, Dept. Chem. and Biochem., BYU, (26).
Awards:
#1 Most-Accessed Article, J. Am. Chem. Soc., April–June 2009.
Top-50 Most Cited Article Award, Tetrahedron 2005–2008.
Research Innovation Award, Research Corporation.
2000–2002 National Institutes of Health Postdoctoral Fellowship.
1995–1998 National Science Foundation Graduate Research Fellowship.

3. - Antimitotic properties
Celogentin C
Isolated from the seeds of Celosia argentea by Kobayashi and co-workers.
Kobayashi isolated eight Celogentin peptides:
- Celogentins A-H
- Bicyclic octapeptides
- Vary according to right-hand structure
- Celogentin C
- Antimitotic properties
- Left-hand ring: Val-Pro-Leu-Val
- Right-hand ring: Trp-Pro-Arg-His

4. Retrosynthesis 1. 2.
Nitro red. 3. + . 4. 5.

5. Synthesis of Modified Tryptophan

6. Stereochemical Analysis of the Asymmetric Phase-Transfer Catalysis
Asymmetric Phase Transfer Catalysis. Edited by Keiji Maruoka Copyright Ó 2008 WILEY-VCH GmbH & Co. KGaA, Weinheim ISBN:
The Basic Principle of Phase-Transfer Catalysis and Some Mechanistic Aspects Takuya Hashimoto and Keiji Maruoka

7. Addition of Modified Leucine-Valine and Radical Conj. Addition

8. Addition of Two Modified Prolines and First Ring Closing

9. Addition of Modified Arginine-Histidine

10. Final Ring Closing

11. Thank you.