Total Synthesis of the Antimitotic Bicyclic Peptide Celogentin C

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Presentation transcript:

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, 1159-1171 Corey Basch Synthesis 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.

- Antimitotic properties 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

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

Synthesis of Modified Tryptophan

Stereochemical Analysis of the Asymmetric Phase-Transfer Catalysis http://www.wiley-vch.de/books/sample/3527318429_c01.pdf 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

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.