TY - JOUR
T1 - Formal Total Synthesis of Manzacidin B via Sequential Diastereodivergent Henry Reaction
AU - Araki, Yuya
AU - Miyoshi, Natsumi
AU - Morimoto, Kazuki
AU - Kudoh, Takayuki
AU - Mizoguchi, Haruki
AU - Sakakura, Akira
N1 - Funding Information:
Financial support for this project was partially provided by a Grant-in-Aid from JSPS KAKENHI (18K05123) and the Naito Foundation. The authors gratefully thank the Division of Instrumental Analysis, Department of Instrumental Analysis & Cryogenics, Advanced Science Research Center, Okayama University for the NMR and HRMS measurements.
Publisher Copyright:
Copyright © 2019 American Chemical Society.
PY - 2020/1/17
Y1 - 2020/1/17
N2 - 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.
AB - 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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U2 - 10.1021/acs.joc.9b02811
DO - 10.1021/acs.joc.9b02811
M3 - Article
C2 - 31850753
AN - SCOPUS:85078509607
SN - 0022-3263
VL - 85
SP - 798
EP - 805
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 2
ER -