Questioning the γ-gauche effect: stereoassignment of 1,3-disubstituted-tetrahydro-β-carbolines using 1H–1H coupling constants-Reference-Cited by-同舟云学术

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Questioning the γ-gauche effect: stereoassignment of 1,3-disubstituted-tetrahydro-β-carbolines using 1H–1H coupling constants

Published:2019 Issue:27 Volume:17 Page:6687-6698
ISSN:1477-0520
Container-title:Organic & Biomolecular Chemistry
language:en
Short-container-title:Org. Biomol. Chem.

Author:

Cagašová Kristýna¹²³⁴^ORCID,Ghavami Maryam¹²³⁴^ORCID,Yao Zhong-Ke¹²³⁴^ORCID,Carlier Paul R.¹²³⁴^ORCID

Affiliation:

1. Department of Chemistry and Virginia Tech Center for Drug Discovery

2. Virginia Tech

3. Blacksburg

4. USA

Abstract

Are γ-gauche interactions in trans-tetrahydro-β-carbolines responsible for upfield ¹³C NMR shifts (Δδ) of C1 and C3 relative to their cis-isomers?

Funder

National Institute of Allergy and Infectious Diseases

Publisher

Royal Society of Chemistry (RSC)

Subject

Organic Chemistry,Physical and Theoretical Chemistry,Biochemistry

Link

http://pubs.rsc.org/en/content/articlepdf/2019/OB/C9OB01139K

Reference60 articles.

1. Pharmacological Importance of Optically Active Tetrahydro-β-carbolines and Synthetic Approaches to Create the C1 Stereocenter

2. Drug to Genome to Drug: Discovery of New Antiplasmodial Compounds

3. The Pictet-Spengler condensation: a new direction for an old reaction

4. Total Synthesis of Sarpagine-Related Bioactive Indole Alkaloids

5. The Discovery of Tadalafil: A Novel and Highly Selective PDE5 Inhibitor. 2: 2,3,6,7,12,12a-hexahydropyrazino[1‘,2‘:1,6]pyrido[3,4-b]indole-1,4-dione Analogues

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