5-Bromo-2-chloro-N-methoxy-N-methylisonicotinamide
CAS Number:
1256790-08-5
Molecular Formula:
C8H8BrClN2O2
Formal total synthesis of salvianolic acid N
Literature Information
Publication Date
2017-12-22
DOI
10.1039/C7OB03025H
Impact Factor
3.876
Authors
Kong Wu, Zhong Pao Xie, Dong-Mei Cui, Chen Zhang
View Original
Abstract
An efficient synthetic pathway for the total synthesis of salvianolic acid N has been reported. The key reaction steps, the Wittig reaction for Z-stereoselectivity and an intramolecular cyclization for a seven membered ring skeleton, have been optimized to improve the synthetic feasibility and provide the best conditions in terms of yield. Moreover, a notable reaction is the reaction of the deprotected allylic group with Pd catalyst. An improved overall yield of 11% has been achieved for salvianolic acid N starting from 3,4-dimethoxybenzaldehyde in 11 steps.
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Source Journal
Organic & Biomolecular Chemistry
CiteScore:
3.4
Self-citation Rate:
10.3%
Articles per Year:
1041
Organic & Biomolecular Chemistry (OBC) publishes original and high impact research and reviews in organic chemistry. We welcome research that shows new or significantly improved protocols or methodologies in total synthesis, synthetic methodology or physical and theoretical organic chemistry as well as research that shows a significant advance in the organic chemistry or molecular design aspects of chemical biology, catalysis, supramolecular and macromolecular chemistry, theoretical chemistry, mechanism-oriented physical organic chemistry, medicinal chemistry or natural products. Articles published in the journal should report new work which makes a highly-significant impact in the field. Routine and incremental work is generally not suitable for publication in the journal. More details about key areas of our scope are below. In all cases authors should include in their article clear rationale for why their research has been carried out.
Recommended Compounds
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Ethanone, 1-[4-chloro-2-(methylthio)-5-pyrimidinyl]-
CAS Number:
66116-82-3
Molecular Formula:
C7H7ClN2OS
methyl 6-bromo-3-formyl-1H-indole-4-carboxylate
CAS Number:
1353636-63-1
Molecular Formula:
C11H8BrNO3
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CAS Number:
142950-86-5
Molecular Formula:
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