Total Synthesis of Lissodendoric Acid A

Francesca M Ippoliti; Laura G Wonilowicz; Nathan J Adamson; Evan R Darzi; Joyann S Donaldson; Daniel J Nasrallah; Milauni M Mehta; Andrew V Kelleghan; K N Houk; Neil K Garg

doi:10.1002/anie.202406676

Total Synthesis of Lissodendoric Acid A

Angew Chem Int Ed Engl. 2024 Aug 5;63(32):e202406676. doi: 10.1002/anie.202406676. Epub 2024 Jul 3.

Authors

Francesca M Ippoliti^{1

2}, Laura G Wonilowicz¹, Nathan J Adamson^{1

3}, Evan R Darzi^{1

4}, Joyann S Donaldson^{1

5}, Daniel J Nasrallah^{1

6}, Milauni M Mehta^{1

7}, Andrew V Kelleghan^{1

8}, K N Houk¹, Neil K Garg¹

Affiliations

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.

PMID: 38695853
PMCID: PMC11461081 (available on 2025-08-05)
DOI: 10.1002/anie.202406676

Abstract

We 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.

Keywords: asymmetric synthesis; bioactive natural product; cyclic allenes; cycloadditions; total synthesis.

Publication types

Research Support, Non-U.S. Gov't
Research Support, N.I.H., Extramural

MeSH terms

Alkaloids* / chemical synthesis
Alkaloids* / chemistry
Molecular Structure
Stereoisomerism

Substances

Alkaloids

Abstract

Publication types

MeSH terms

Substances

Grants and funding