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Formal Total Synthesis of Manzacidin B via Sequential Diastereodivergent Henry Reaction. | LitMetric

Formal Total Synthesis of Manzacidin B via Sequential Diastereodivergent Henry Reaction.

J Org Chem

Division of Applied Chemistry, Graduate School of Natural Science and Technology , Okayama University, 3-1-1 Tsushima-naka , Kita-ku, Okayama 700-8530 , Japan.

Published: January 2020

A formal total synthesis of manzacidin B is described. β,β-Disubstituted γ-hydroxy-β-aminoalcohol, the key structure of manzacidin B, is stereoselectively constructed via sequential Henry reactions. By taking advantage of noncovalent interactions, such as intramolecular hydrogen bonding and chelation, we could diastereodivergently control the stereoselectivity of the Henry reaction.

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http://dx.doi.org/10.1021/acs.joc.9b02811DOI Listing

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