Total synthesis of (±)-decursivine via BINOL-phosphoric acid catalyzed tandem oxidative cyclization

Prakash T Parvatkar; Eugene S Smotkin; Roman Manetsch

doi:10.1038/s41598-021-99064-8

Total synthesis of (±)-decursivine via BINOL-phosphoric acid catalyzed tandem oxidative cyclization

Sci Rep. 2021 Oct 7;11(1):19915. doi: 10.1038/s41598-021-99064-8.

Authors

Prakash T Parvatkar¹, Eugene S Smotkin¹, Roman Manetsch^{2

3}

Affiliations

¹ Department of Chemistry and Chemical Biology, Northeastern University, 102 Hurtig Hall, 360 Huntington Avenue, Boston, MA, 02115, USA.
² Department of Chemistry and Chemical Biology, Northeastern University, 102 Hurtig Hall, 360 Huntington Avenue, Boston, MA, 02115, USA. [email protected].
³ Department of Pharmaceutical Sciences, Northeastern University, 102 Hurtig Hall, 360 Huntington Avenue, Boston, MA, 02115, USA. [email protected].

Abstract

The synthesis of tetracyclic indole alkaloid (±)-decursivine was accomplished using BINOL-phosphoric acid catalyzed tandem oxidative cyclization as a key step with (bis(trifluoroacetoxy)iodo)benzene (PIFA) as an oxidizing agent. This represents one of the shortest and highest yielding routes for the synthesis of (±)-decursivine from readily available starting materials.

Publication types

Research Support, N.I.H., Extramural

MeSH terms

Catalysis
Chemistry Techniques, Synthetic
Cyclization
Indole Alkaloids / chemical synthesis*
Indole Alkaloids / chemistry
Molecular Structure
Naphthols / chemistry*
Oxidation-Reduction*
Phosphoric Acids / chemistry*

Substances

BINOL, naphthol
Indole Alkaloids
Naphthols
Phosphoric Acids
decursivine
phosphoric acid

Abstract

Publication types

MeSH terms

Substances

Grants and funding