Synthesis of 1,2-diaminotruxinic δ-cyclobutanes by BF<sub>3</sub>-controlled [2 + 2]-photocycloaddition of 5(4<i>H</i>)-oxazolones and stereoselective expansion of δ-cyclobutanes to give highly substituted pyrrolidine-2,5-dicarboxylates-Reference-Cited by-同舟云学术

Synthesis of 1,2-diaminotruxinic δ-cyclobutanes by BF₃-controlled [2 + 2]-photocycloaddition of 5(4H)-oxazolones and stereoselective expansion of δ-cyclobutanes to give highly substituted pyrrolidine-2,5-dicarboxylates

Published:2023 Issue:15 Volume:21 Page:3203-3213
ISSN:1477-0520
Container-title:Organic & Biomolecular Chemistry
language:en
Short-container-title:Org. Biomol. Chem.

Author:

Sierra Sonia¹^ORCID,López Rosa²^ORCID,Gómez-Bengoa Enrique²^ORCID,Falvello Larry R.³^ORCID,Urriolabeitia Esteban P.¹^ORCID

Affiliation:

1. Instituto de Síntesis Química y Catálisis Homogénea, ISQCH (CSIC - Universidad de Zaragoza), 50009 Zaragoza, Spain

2. Departamento de Química Orgánica I, Universidad del País Vasco, UPV-EHU, CP-20080 Donostia-San Sebastián, Spain

3. Instituto de Nanociencia y Materiales de Aragón, INMA (CSIC - Universidad de Zaragoza), 50009 Zaragoza, Spain

Abstract

Ru-sensitized [2+2]-photocycloaddition of oxazolones 1 in presence of BF3gives selectively the δ-1,2-diaminotruxinic acids 2. Heating of 2 with NaOMe promotes an unprecedented cyclobutane ring expansion, giving the highly substituted pyrrolidines 3.

Funder

Ministerio de Ciencia e Innovación

European Regional Development Fund

Gobierno de Aragón

Publisher

Royal Society of Chemistry (RSC)

Subject

Organic Chemistry,Physical and Theoretical Chemistry,Biochemistry

Link

http://pubs.rsc.org/en/content/articlepdf/2023/OB/D3OB00284E

Reference70 articles.

1. Amino Acids, Peptides and Proteins in Organic Chemistry, Volumes 1–5 (Volume 1: Origins and Synthesis of Amino Acids; Volume 2: Modified Amino Acids, Organocatalysis and Enzymes; Volume 3: Building Blocks, Catalysis and Coupling Chemistry; Volume 4: Protection Reactions, Medicinal Chemistry, Combinatorial Synthesis; Volume 5: Analysis and Function of Amino Acids and Peptides) , ed. A. B. Hughes , Wiley–VCH Verlag GmbH & Co. KGaA , 2009–2011

2. Amino Acids, Peptides and Proteins , ed. M. Ryadnov and F. Hudecz , Royal Society of Chemistry , 2021 , vol. 44

3. Amino Acid Metabolism as a Target for Breast Cancer Imaging

4. 18F-Fluciclovine PET for Assessment of Prostate Cancer with Histopathology as Reference Standard