Adaptation of a Small-Molecule Hydrogen-Bond Donor Catalyst to an Enantioselective Hetero-Diels–Alder Reaction Hypothesized for Brevianamide Biosynthesis | Zendy

Daniel J. Sprague | Zendy; Benjamin M. Nugent | Zendy; Ryan A. Yoder | Zendy; Brandon Vara | Zendy; Jeffrey N. Johnston | Zendy

Open Access

Adaptation of a Small-Molecule Hydrogen-Bond Donor Catalyst to an Enantioselective Hetero-Diels–Alder Reaction Hypothesized for Brevianamide Biosynthesis

Author(s) -

Daniel J. Sprague,

Benjamin M. Nugent,

Ryan A. Yoder,

Brandon Vara,

Jeffrey N. Johnston

Publication year - 2015

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/ol503626w

Subject(s) - chemistry , enantioselective synthesis , intramolecular force , catalysis , biosynthesis , molecule , hydrogen bond , stereoisomerism , stereochemistry , combinatorial chemistry , organic chemistry , enzyme

Chiral diamine-derived hydrogen-bond donors were evaluated for their ability to effect stereocontrol in an intramolecular hetero-Diels-Alder (HDA) reaction hypothesized in the biosynthesis of brevianamides A and B. Collectively, these results provide proof of principle that small-molecule hydrogen-bond catalysis, if even based on a hypothetical biosynthesis construct, holds significant potential within enantioselective natural product synthesis.

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