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Total Synthesis of (-)-Cyanthiwigin F: Enantioselective Alkylation Method

Prof. Brain M. Stoltz's groundbreaking work on the total synthesis of Cyanthiwigin F, a bioactive molecule with cytotoxic properties against tumour cells. The synthesis involves enantioselective double alkylation and ring-closing metathesis.

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Total Synthesis of (-)-Cyanthiwigin F: Enantioselective Alkylation Method

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  1. The total synthesis of (-)-cyanthiwigin F by means of double catalytic enantioselective alkylation J.A. Enquist, Jr., B.M. Stoltz, Nature 2008,453,1228 Presented by Vijayarajan Devannah on 5/7/2013

  2. About Professor Brain M. Stoltz Education and Professional Experience • B.S., Indiana University of Pennsylvania 1993 • Ph.D., Yale University (John Wood) 1997 • NIH posdoctoral Fellow, Harvard University ( E. J. Corey ) 1998-2000 • Currently professor of chemistry at California Institute of Technology, Pasadena. Honors and Awards • Camille and Henry Dreyfus New Faculty Award, 2000 • Glaxosmithkline Chemistry scholar Award 2002 and 2003 • Amgen Young investigator Award 2003 • Arthur C Cope Scholar Award from the American Chemical Society 2005 • E J Corey Award for outstanding original contribution in the organic synthesis by a young investigator, 2009 • H.C. Brown Lecturer in Organic Chemistry, Purdue University, Indiana, 2011

  3. About Cyanthiwigin F • Isolated from the sea sponge Myrmekioderma styx, • Cyanthiwigin F is one of 30 known cyanthiwigin natural products, which belongs to a larger class of bioactive molecules known as cyathins. • Cyathins display a wide range of biological properties including antimicrobial activity, antineoplastic actions, stimulation of nerve growth factor synthesis, and κ-opioid receptor agonism. • Cyanthiwigin F exhibits cytotoxicity activity against human primary tumour cells with a half-maximal inhibitory concentration of 3.1μg/ml. Synthetic Challenges posed by Cyanthiwigin F • Construction of two all-carbon quaternary stereocentres at the A-B and B-C ring juncture. • Fused 5-6-7 ring system.

  4. Retrosynthesis

  5. Synthesis of diketone through stereoablative and enantioselective double allylation

  6. Stereochemical analysis of bis(β-ketoester)

  7. Synthesis of bicyclic aldehyde through olefin metathesis

  8. Final Stages and completion of total synthesis of cyanthiwigin F

  9. Conclusion • They achieved the catalytic enantioselective synthesis of the cyanthin diterpenoid (-)-cyanthiwigin F in 10 steps. • Total yield is 1.8% • Introduction of two chiral centers in one pot with excellent ee • Tandem ring-closing and cross metathesis • No protection and Deprotection involved.

  10. Thank You

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