Synthesis of Complex Hexacyclic Compounds via a Tandem Rh(II)-Catalyzed Double-Cyclopropanation/Cope Rearrangement/Diels–Alder Reaction

[Image: see text] Treatment of (E)-1-(methoxymethylene)-1,2,3,4-tetrahydronaphthalene with styryl diazoacetates in the presence of catalytic amounts of the dirhodium complex Rh(2)(S-DOSP)(4) provides a highly enantioenriched hexacyclic product with 10 new stereogenic centers. The transformation proc...

Descripción completa

Detalles Bibliográficos
Autores principales: Spangler, Jillian E., Lian, Yajing, Raikar, Sandeep N., Davies, Huw M. L.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2014
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4168775/
https://www.ncbi.nlm.nih.gov/pubmed/25208337
http://dx.doi.org/10.1021/ol502257d
_version_ 1782335616586874880
author Spangler, Jillian E.
Lian, Yajing
Raikar, Sandeep N.
Davies, Huw M. L.
author_facet Spangler, Jillian E.
Lian, Yajing
Raikar, Sandeep N.
Davies, Huw M. L.
author_sort Spangler, Jillian E.
collection PubMed
description [Image: see text] Treatment of (E)-1-(methoxymethylene)-1,2,3,4-tetrahydronaphthalene with styryl diazoacetates in the presence of catalytic amounts of the dirhodium complex Rh(2)(S-DOSP)(4) provides a highly enantioenriched hexacyclic product with 10 new stereogenic centers. The transformation proceeds by a cascade sequence starting with a double cyclopropanation of a benzene ring, followed by a Cope rearrangement of a divinylcyclopropane and then an intramolecular Diels–Alder cycloaddition.
format Online
Article
Text
id pubmed-4168775
institution National Center for Biotechnology Information
language English
publishDate 2014
publisher American Chemical Society
record_format MEDLINE/PubMed
spelling pubmed-41687752015-09-10 Synthesis of Complex Hexacyclic Compounds via a Tandem Rh(II)-Catalyzed Double-Cyclopropanation/Cope Rearrangement/Diels–Alder Reaction Spangler, Jillian E. Lian, Yajing Raikar, Sandeep N. Davies, Huw M. L. Org Lett [Image: see text] Treatment of (E)-1-(methoxymethylene)-1,2,3,4-tetrahydronaphthalene with styryl diazoacetates in the presence of catalytic amounts of the dirhodium complex Rh(2)(S-DOSP)(4) provides a highly enantioenriched hexacyclic product with 10 new stereogenic centers. The transformation proceeds by a cascade sequence starting with a double cyclopropanation of a benzene ring, followed by a Cope rearrangement of a divinylcyclopropane and then an intramolecular Diels–Alder cycloaddition. American Chemical Society 2014-09-10 2014-09-19 /pmc/articles/PMC4168775/ /pubmed/25208337 http://dx.doi.org/10.1021/ol502257d Text en Copyright © 2014 American Chemical Society Terms of Use (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html)
spellingShingle Spangler, Jillian E.
Lian, Yajing
Raikar, Sandeep N.
Davies, Huw M. L.
Synthesis of Complex Hexacyclic Compounds via a Tandem Rh(II)-Catalyzed Double-Cyclopropanation/Cope Rearrangement/Diels–Alder Reaction
title Synthesis of Complex Hexacyclic Compounds via a Tandem Rh(II)-Catalyzed Double-Cyclopropanation/Cope Rearrangement/Diels–Alder Reaction
title_full Synthesis of Complex Hexacyclic Compounds via a Tandem Rh(II)-Catalyzed Double-Cyclopropanation/Cope Rearrangement/Diels–Alder Reaction
title_fullStr Synthesis of Complex Hexacyclic Compounds via a Tandem Rh(II)-Catalyzed Double-Cyclopropanation/Cope Rearrangement/Diels–Alder Reaction
title_full_unstemmed Synthesis of Complex Hexacyclic Compounds via a Tandem Rh(II)-Catalyzed Double-Cyclopropanation/Cope Rearrangement/Diels–Alder Reaction
title_short Synthesis of Complex Hexacyclic Compounds via a Tandem Rh(II)-Catalyzed Double-Cyclopropanation/Cope Rearrangement/Diels–Alder Reaction
title_sort synthesis of complex hexacyclic compounds via a tandem rh(ii)-catalyzed double-cyclopropanation/cope rearrangement/diels–alder reaction
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4168775/
https://www.ncbi.nlm.nih.gov/pubmed/25208337
http://dx.doi.org/10.1021/ol502257d
work_keys_str_mv AT spanglerjilliane synthesisofcomplexhexacycliccompoundsviaatandemrhiicatalyzeddoublecyclopropanationcoperearrangementdielsalderreaction
AT lianyajing synthesisofcomplexhexacycliccompoundsviaatandemrhiicatalyzeddoublecyclopropanationcoperearrangementdielsalderreaction
AT raikarsandeepn synthesisofcomplexhexacycliccompoundsviaatandemrhiicatalyzeddoublecyclopropanationcoperearrangementdielsalderreaction
AT davieshuwml synthesisofcomplexhexacycliccompoundsviaatandemrhiicatalyzeddoublecyclopropanationcoperearrangementdielsalderreaction

Ejemplares similares