Site-selectivity control in hetero-Diels–Alder reactions of methylidene derivatives of lawsone through modification of the reactive carbonyl group: an experimental and theoretical study-Reference-Cited by-同舟云学术

Site-selectivity control in hetero-Diels–Alder reactions of methylidene derivatives of lawsone through modification of the reactive carbonyl group: an experimental and theoretical study

Published:2019 Issue:3 Volume:17 Page:692-702
ISSN:1477-0520
Container-title:Organic & Biomolecular Chemistry
language:en
Short-container-title:Org. Biomol. Chem.

Author:

Tsanakopoulou Maria¹²³⁴⁵^ORCID,Tsovaltzi Erifili¹²³⁴⁵,Tzani Marina A.¹²³⁴⁵^ORCID,Selevos Periklis¹²³⁴⁵,Malamidou-Xenikaki Elizabeth¹²³⁴⁵^ORCID,Bakalbassis Evangelos G.⁶²³⁴⁵,Domingo Luis R.⁷⁸⁹¹⁰^ORCID

Affiliation:

1. Laboratory of Organic Chemistry

2. School of Chemistry

3. Faculty of Sciences

4. Aristotle University of Thessaloniki

5. 54124 Thessaloniki

6. Laboratory of Applied Quantum Chemistry

7. Universidad de Valencia

8. Departamento de Química Orgánica

9. E-46100 Burjassot

10. Spain

Abstract

Selective monoacetalization of lawsone inverts the site-selectivity of the Diels–Alder reactions of its alkylidene derivatives favoring the protected β-lapachone derivatives.

Publisher

Royal Society of Chemistry (RSC)

Subject

Organic Chemistry,Physical and Theoretical Chemistry,Biochemistry

Link

http://pubs.rsc.org/en/content/articlepdf/2019/OB/C8OB02383B

Reference54 articles.

1. R. H. Thomson , Naturally Occurring Quinones IV. Recent Advances , Blackie A&P , London , 1997

2. Lawsone in organic synthesis

3. A preparative synthesis of lapachol and related naphthoquinones

4. Facile and highly efficient method for the C-alkylation of 2-hydroxy-1,4-naphthoquinone to nitroalkenes under catalyst-free ‘on water’ conditions

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