Total Synthesis of the Antimitotic Bicyclic PeptideCelogentin C

Bing Ma, Biplab Banerjee, Dmitry N. Litvinov, Liwen He, and Steven L. Castle J. Am. Chem. Soc. 2010, 132, 1159-1171

Corey BaschSynthesis Presentation

3/19/13

Steven L. Castle

CV

1986-89: Summer research assistant, U. of South Florida, (4).advisor: Raymond N. Castle

1992-95: B.S. Chemistry, Brigham Young University, (1).advisor: Jerald S. Bradshaw

1995-2000: PhD Chemistry, Scripps Research Institute, (12). advisor: Dale. L. Boger

2000-02: Assistant Professor, Dept. Chemistry and Biochemistry, Brigham Young University, (26).

2008-Present: Associate Professor, Dept. Chem. and Biochem., BYU, (26).

Awards:

2009 #1 Most-Accessed Article, J. Am. Chem. Soc., April–June 2009.

2008 Top-50 Most Cited Article Award, Tetrahedron 2005–2008.

2004 Research Innovation Award, Research Corporation.

2000–2002 National Institutes of Health Postdoctoral Fellowship.

1995–1998 National Science Foundation Graduate Research Fellowship.

Celogentin C

2001 - 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

+ 1. 2.Nitro red.

.

3.

5. 4.

Retrosynthesis

Synthesis of Modified Tryptophan

Asymmetric Phase Transfer Catalysis. Edited by Keiji Maruoka Copyright Ó 2008 WILEY-VCH GmbH & Co. KGaA, Weinheim ISBN: 978-3-527-31842-1

The Basic Principle of Phase-Transfer Catalysis and Some Mechanistic Aspects Takuya Hashimoto and Keiji Maruoka

http://www.wiley-vch.de/books/sample/3527318429_c01.pdf

Stereochemical Analysis of the Asymmetric Phase-Transfer Catalysis

Addition of Modified Leucine-Valine and Radical Conj. Addition

Addition of Two Modified Prolines and First Ring Closing

Addition of Modified Arginine-Histidine

Final Ring Closing

Thank you.