Total Synthesis of Lissodendoric Acid A

Author:

Ippoliti Francesca M.12ORCID,Wonilowicz Laura G.1ORCID,Adamson Nathan J.13ORCID,Darzi Evan R.14ORCID,Donaldson Joyann S.15,Nasrallah Daniel J.16ORCID,Mehta Milauni M.17,Kelleghan Andrew V.18,Houk K. N.1,Garg Neil K.1ORCID

Affiliation:

1. Department of Chemistry and Biochemistry University of California, Los Angeles Los Angeles CA 90095 USA

2. Department of Chemistry Hamline University St. Paul Minnesota 55104 USA

3. Department of Discovery Chemistry Genentech, Inc. South San Francisco CA 94080 USA

4. ElectraTect, Inc. Phoenix AZ 85004 USA

5. Pfizer Oncology Medicinal Chemistry San Diego CA 92121 USA

6. Department of Chemistry Roanoke College Salem Virginia 24153 USA

7. Small Molecule Therapeutic Discovery Amgen Research Amgen Inc. Thousand Oaks CA 91320 USA

8. Gilead Sciences Medicinal Chemistry Foster City CA 94404 USA

Abstract

AbstractWe describe a full account of our synthetic strategy leading to the first total synthesis of the manzamine alkaloid lissodendoric acid A . These efforts demonstrate that strained cyclic allenes are valuable synthetic building blocks and can be employed efficiently in total synthesis.

Funder

National Institute of General Medical Sciences

National Science Foundation Graduate Research Fellowship Program

Division of Chemistry

National Center for Research Resources

National Institutes of Health

National Science Foundation

Publisher

Wiley

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