Stereoselective Synthesis of Tropanes via a Retro-6 p Electrocyclic Ring-Opening / Huisgen [3+2]-Cycloaddition Cascade of Monocyclopropanated Heterocycles. Stereoselektive Synthese von Tropanen über eine 6π-elektrocyclische Ringöffnung/ Huisgen-[3+2]-Cycloadditionskaskade von monocyclopropanierten Heterocyclen

URN to cite this document:

urn:nbn:de:bvb:355-epub-445791 Copy

DOI to cite this document:

10.5283/epub.44579 Copy

Sonnleitner, Carina M. ; Park, Saerom ; Eckl, Robert ; Ertl, Thomas ; Reiser, Oliver

Preview	License: Creative Commons Attribution Non-commercial No Derivatives 4.0 PDF - Published Version in: internat. Ausgabe (1MB)
Preview	License: Creative Commons Attribution 4.0 PDF - Published Version in: dtsch. Ausgabe (1MB)

Date of publication of this fulltext: 25 Jan 2021 08:02

---

Alternative links to fulltext:DOIPublisherPublisher

---

Details

Item type:	Thesis (UNSPECIFIED)
Journal or Publication Title:	Angewandte Chemie International Edition
Publisher:	WILEY-V C H VERLAG GMBH
Place of Publication:	WEINHEIM
Volume:	59
Page Range:	pp. 18110-18115
Date:	2020
Institutions:	Chemistry and Pharmacy > Institut für Organische Chemie Chemistry and Pharmacy > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Oliver Reiser
Identification Number:	Value Type 10.1002/anie.202006030 DOI
Keywords:	COCAINE C-1 ANALOGS; ENANTIOSELECTIVE SYNTHESIS; FUNCTIONALIZED TROPANES; CYCLOADDITION REACTIONS; ENANTIOMERICALLY PURE; ASYMMETRIC-SYNTHESIS; BINDING-AFFINITY; OPIOID RECEPTORS; NATURAL-PRODUCTS; DOPAMINE; bicyclo[3; 2; 1]octanes; cocaine analogues; furans and pyrroles; isoquinuclidines; microwave-assisted [3+2]-cycloaddition; tropanes
Dewey Decimal Classification:	500 Science > 540 Chemistry & allied sciences
Status:	Published
Refereed:	Yes, this version has been refereed
Created at the University of Regensburg:	Yes
Item ID:	44579

Preview: in: internat. Ausgabe

Preview: in: dtsch. Ausgabe

Indexed in

Web of Science

Export bibliographical data

ASCII CitationAtomBibTeXData Cite XMLDataCite XML OAIDublin CoreEndNoteHTML CitationJSON LDMETSMODSOpenAPCRDF+N-TriplesRDF+N3RDF+XMLReferReference ManagerSimple MetadataXMLxMetaDissPlus

---

Abstract

The synthesis of tropanes via a microwave-assisted, stereoselective 6 pi-electrocyclic ring-opening/ Huisgen [3+2]-cycloaddition cascade of cyclopropanated pyrrole and furan derivatives with electron-deficient dipolarophiles is demonstrated. Starting from furans or pyrroles, 8-aza- and 8-oxabicyclo[3.2.1]octanes are accessible in two steps in dia- and enantioselective pure form, being versatile ...

Abstract

The synthesis of tropanes via a microwave-assisted, stereoselective 6 pi-electrocyclic ring-opening/ Huisgen [3+2]-cycloaddition cascade of cyclopropanated pyrrole and furan derivatives with electron-deficient dipolarophiles is demonstrated. Starting from furans or pyrroles, 8-aza- and 8-oxabicyclo[3.2.1]octanes are accessible in two steps in dia- and enantioselective pure form, being versatile building blocks for the synthesis of pharmaceutically relevant targets, especially for new cocaine analogues bearing various substituents at the C-6/C-7 positions of the tropane ring system. Moreover, the 2-azabicyclo[2.2.2]octane core (isoquinuclidines), being prominently represented in many natural and pharmaceutical products, is accessible via this approach.

---

---

Metadata last modified: 29 Sep 2021 07:42

Owner only: item control page

Download Statistics

Download Statistics

Download Statistics

Download Statistics

Downloads

Downloads per month over past year

Altmetric

Altmetric

Altmetric

Alternative Statistics (altmetrics)

More literature (via CORE)

More literature (via CORE)

More literature (via CORE)

More literature (via CORE)