Asymmetric Total Synthesis of Caribenol A Author: Zhen Yang J. Am. Chem. Soc. 2010, 132, 13608

Asymmetric Total Synthesis of Caribenol AAuthor: Zhen YangJ. Am. Chem. Soc. 2010, 132, 13608 Presented by Daniel Roberts April 6th 2014

Zhen Yang Degrees • 1978-82 B.S. Pharmaceutical Chemistry, Shenyang College of Pharmacy • 1983-86 M.S. Pharmaceutical Chemistry, Shenyang College of Pharmacy • 1989-92 Ph.D. Chemistry, Chinese University of Hong Kong Academic Career • 1992-95 Postdoctoral Fellow, Dept. of Chemistry, Scripps Research Inst. • 1995-98 Assistant Professor, Dept of Chemistry, Scripps • 2001-05 Institute Fellow, Dept. Cell Biology, Harvard Medical School • 2002- Present, Changjiang Professor of Chemistry, Peking University Honors • 2000 The National Science Fund for Distinguished Young Investigator Award (abroad), NSF of China (and 2004) • 2005 Eli Lilly Scientific Excellence Award (China) • 2009 Baogang Distinguished Teaching Award of Peking University • 2010 Wuxi Pharma Life Science Excellence Award (Golden Metal)

Caribenol A • First isolated in 2007 from West Indian gorgonian octocoral • Shows strong inhibitory activity against mycobacterium tuberculosis (H37Rv), which causes tuberculosis. • Caribenol A has an unprecedented tricarbocyclic ring system in that all three methyl groups are cis and contains a 5 hydroxyfurnan motif • Chemically scarce

RetroSynthesis Carbenol A

Forward Synthesis t-BuLi, Et2O -78c PCC, CH2Cl2 LiBEt3H,THF TBSOTf, Et3N

Forward Synthesis Dibal, DCM -78c n-BuLI, THF -78c DMP, NaHCO3 rt DMP, NaHCO3 rt

Forward Synthesis Diels - Alder BHT 120c Rh(PPh3)3Cl, H2 HF/Py, THF

Forward Synthesis NaBH4 CeCl3 7H2O EtOH TPAP, NMO, 4 A MS, DCM 0c KHMDS, THF Comins Reagent Pd/C, H2,THF -78c

Forward Synthesis Pd(PPh3)4, Me2Zn, THF rt O2, DMF, K2CO3 P(OEt)3 60c, 80 hr

Finished

Asymmetric Total Synthesis of Caribenol A Author: Zhen Yang J. Am. Chem. Soc. 2010, 132, 13608

Asymmetric Total Synthesis of Caribenol A Author: Zhen Yang J. Am. Chem. Soc. 2010, 132, 13608

Presentation Transcript

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