Combined Enzyme- and Transition Metal-Catalyzed Strategy for the Enantioselective Syntheses of Nitrogen Heterocycles: (−)-Coniine, DAB-1, and Nectrisine | Zendy

Donald R. Deardorff | Zendy; Scott W. Niman | Zendy; Mark I. Paulsen | Zendy; Anasheh Sookezian | Zendy; Meghan Whalen | Zendy; Christopher J. Finlayson | Zendy; Collrane Frivold | Zendy; Hilary C. Brown | Zendy; Jeffrey S. Can | Zendy

Open Access

Combined Enzyme- and Transition Metal-Catalyzed Strategy for the Enantioselective Syntheses of Nitrogen Heterocycles: (−)-Coniine, DAB-1, and Nectrisine

Author(s) -

Donald R. Deardorff,

Scott W. Niman,

Mark I. Paulsen,

Anasheh Sookezian,

Meghan Whalen,

Christopher J. Finlayson,

Collrane Frivold,

Hilary C. Brown,

Jeffrey S. Can

Publication year - 2020

Publication title -

acs omega

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.779

H-Index - 40

ISSN - 2470-1343

DOI - 10.1021/acsomega.9b03990

Subject(s) - enantioselective synthesis , pyrrolidine , chemistry , stereocenter , allylic rearrangement , catalysis , piperidine , stereoselectivity , stereochemistry , metathesis , hydrocyanation , pictet–spengler reaction , substrate (aquarium) , combinatorial chemistry , organic chemistry , polymer , oceanography , geology , polymerization

The enantioselective syntheses of (-)-coniine, DAB-1, and nectrisine have been developed, utilizing a complementary strategy of enzyme- and transition metal-catalyzed reactions. The initial stereocenter was set with >99% enantioselectivity via an enzyme-catalyzed hydrocyanation reaction. Substrate incompatibilities with the natural enzyme were overcome by tactical utilization of ruthenium-catalyzed olefin metathesis to functionalize an enzyme-derived ( R )-allylic fragment. The piperidine and pyrrolidine alkaloid natural products were obtained by a route that leveraged regio- and stereoselective palladium-catalyzed 1,3-substitutive reactions.

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