Studies on C(20)-Diterpenoid Alkaloids: Synthesis of the Hetidine Framework and Its Application to the Synthesis of Dihydronavirine and the Atisine Skeleton

[Image: see text] The full details of a synthesis of the hetidine framework of the C(20)-diterpenoid alkaloids and its conversion to the atisine core structure are reported. The application of the hetidine framework to the synthesis of dihydronavirine, which is the formal reduction product of the na...

Descripción completa

Detalles Bibliográficos
Autores principales: Hamlin, Amy M., Lapointe, David, Owens, Kyle, Sarpong, Richmond
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2014
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4120980/
https://www.ncbi.nlm.nih.gov/pubmed/25004408
http://dx.doi.org/10.1021/jo501214b
_version_ 1782329158294044672
author Hamlin, Amy M.
Lapointe, David
Owens, Kyle
Sarpong, Richmond
author_facet Hamlin, Amy M.
Lapointe, David
Owens, Kyle
Sarpong, Richmond
author_sort Hamlin, Amy M.
collection PubMed
description [Image: see text] The full details of a synthesis of the hetidine framework of the C(20)-diterpenoid alkaloids and its conversion to the atisine core structure are reported. The application of the hetidine framework to the synthesis of dihydronavirine, which is the formal reduction product of the natural product navirine, is also described. Key to the success of these studies is the use of a Ga(III)-catalyzed cycloisomerization reaction of alkynylindenes to prepare a [6–7–6] framework that was advanced to the hetidine skeleton. Furthermore, a Michael/aldol sequence was developed for the construction of the bicyclo[2.2.2] framework that is characteristic of the hetidines and atisines.
format Online
Article
Text
id pubmed-4120980
institution National Center for Biotechnology Information
language English
publishDate 2014
publisher American Chemical Society
record_format MEDLINE/PubMed
spelling pubmed-41209802015-07-08 Studies on C(20)-Diterpenoid Alkaloids: Synthesis of the Hetidine Framework and Its Application to the Synthesis of Dihydronavirine and the Atisine Skeleton Hamlin, Amy M. Lapointe, David Owens, Kyle Sarpong, Richmond J Org Chem [Image: see text] The full details of a synthesis of the hetidine framework of the C(20)-diterpenoid alkaloids and its conversion to the atisine core structure are reported. The application of the hetidine framework to the synthesis of dihydronavirine, which is the formal reduction product of the natural product navirine, is also described. Key to the success of these studies is the use of a Ga(III)-catalyzed cycloisomerization reaction of alkynylindenes to prepare a [6–7–6] framework that was advanced to the hetidine skeleton. Furthermore, a Michael/aldol sequence was developed for the construction of the bicyclo[2.2.2] framework that is characteristic of the hetidines and atisines. American Chemical Society 2014-07-08 2014-08-01 /pmc/articles/PMC4120980/ /pubmed/25004408 http://dx.doi.org/10.1021/jo501214b Text en Copyright © 2014 American Chemical Society Terms of Use (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html)
spellingShingle Hamlin, Amy M.
Lapointe, David
Owens, Kyle
Sarpong, Richmond
Studies on C(20)-Diterpenoid Alkaloids: Synthesis of the Hetidine Framework and Its Application to the Synthesis of Dihydronavirine and the Atisine Skeleton
title Studies on C(20)-Diterpenoid Alkaloids: Synthesis of the Hetidine Framework and Its Application to the Synthesis of Dihydronavirine and the Atisine Skeleton
title_full Studies on C(20)-Diterpenoid Alkaloids: Synthesis of the Hetidine Framework and Its Application to the Synthesis of Dihydronavirine and the Atisine Skeleton
title_fullStr Studies on C(20)-Diterpenoid Alkaloids: Synthesis of the Hetidine Framework and Its Application to the Synthesis of Dihydronavirine and the Atisine Skeleton
title_full_unstemmed Studies on C(20)-Diterpenoid Alkaloids: Synthesis of the Hetidine Framework and Its Application to the Synthesis of Dihydronavirine and the Atisine Skeleton
title_short Studies on C(20)-Diterpenoid Alkaloids: Synthesis of the Hetidine Framework and Its Application to the Synthesis of Dihydronavirine and the Atisine Skeleton
title_sort studies on c(20)-diterpenoid alkaloids: synthesis of the hetidine framework and its application to the synthesis of dihydronavirine and the atisine skeleton
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4120980/
https://www.ncbi.nlm.nih.gov/pubmed/25004408
http://dx.doi.org/10.1021/jo501214b
work_keys_str_mv AT hamlinamym studiesonc20diterpenoidalkaloidssynthesisofthehetidineframeworkanditsapplicationtothesynthesisofdihydronavirineandtheatisineskeleton
AT lapointedavid studiesonc20diterpenoidalkaloidssynthesisofthehetidineframeworkanditsapplicationtothesynthesisofdihydronavirineandtheatisineskeleton
AT owenskyle studiesonc20diterpenoidalkaloidssynthesisofthehetidineframeworkanditsapplicationtothesynthesisofdihydronavirineandtheatisineskeleton
AT sarpongrichmond studiesonc20diterpenoidalkaloidssynthesisofthehetidineframeworkanditsapplicationtothesynthesisofdihydronavirineandtheatisineskeleton

Ejemplares similares