Stereodivergent Approach to the Avermectins Based on “Super Silyl” Directed Aldol Reactions

[Image: see text] A stereodivergent approach to the spiroketal fragment of the avermectins is described. The strategy utilizes a sequence of three aldol reactions directed by the tris(trimethylsilyl)silyl “super silyl” group. Central to this strategy is that each aldol reaction can be controlled to...

Descripción completa

Detalles Bibliográficos
Autores principales: Brady, Patrick B., Oda, Susumu, Yamamoto, Hisashi
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2014
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4120983/
https://www.ncbi.nlm.nih.gov/pubmed/25025525
http://dx.doi.org/10.1021/ol501327g
_version_ 1782329158734446592
author Brady, Patrick B.
Oda, Susumu
Yamamoto, Hisashi
author_facet Brady, Patrick B.
Oda, Susumu
Yamamoto, Hisashi
author_sort Brady, Patrick B.
collection PubMed
description [Image: see text] A stereodivergent approach to the spiroketal fragment of the avermectins is described. The strategy utilizes a sequence of three aldol reactions directed by the tris(trimethylsilyl)silyl “super silyl” group. Central to this strategy is that each aldol reaction can be controlled to allow access to either diastereomer in high stereoselectivity, thereby affording 16 stereoisomers along the same linear skeleton. The aldol products can be transformed into spiroketals, including an advanced intermediate in the total synthesis of avermectin A1a.
format Online
Article
Text
id pubmed-4120983
institution National Center for Biotechnology Information
language English
publishDate 2014
publisher American Chemical Society
record_format MEDLINE/PubMed
spelling pubmed-41209832015-07-15 Stereodivergent Approach to the Avermectins Based on “Super Silyl” Directed Aldol Reactions Brady, Patrick B. Oda, Susumu Yamamoto, Hisashi Org Lett [Image: see text] A stereodivergent approach to the spiroketal fragment of the avermectins is described. The strategy utilizes a sequence of three aldol reactions directed by the tris(trimethylsilyl)silyl “super silyl” group. Central to this strategy is that each aldol reaction can be controlled to allow access to either diastereomer in high stereoselectivity, thereby affording 16 stereoisomers along the same linear skeleton. The aldol products can be transformed into spiroketals, including an advanced intermediate in the total synthesis of avermectin A1a. American Chemical Society 2014-07-15 2014-08-01 /pmc/articles/PMC4120983/ /pubmed/25025525 http://dx.doi.org/10.1021/ol501327g Text en Copyright © 2014 American Chemical Society Terms of Use (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html)
spellingShingle Brady, Patrick B.
Oda, Susumu
Yamamoto, Hisashi
Stereodivergent Approach to the Avermectins Based on “Super Silyl” Directed Aldol Reactions
title Stereodivergent Approach to the Avermectins Based on “Super Silyl” Directed Aldol Reactions
title_full Stereodivergent Approach to the Avermectins Based on “Super Silyl” Directed Aldol Reactions
title_fullStr Stereodivergent Approach to the Avermectins Based on “Super Silyl” Directed Aldol Reactions
title_full_unstemmed Stereodivergent Approach to the Avermectins Based on “Super Silyl” Directed Aldol Reactions
title_short Stereodivergent Approach to the Avermectins Based on “Super Silyl” Directed Aldol Reactions
title_sort stereodivergent approach to the avermectins based on “super silyl” directed aldol reactions
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4120983/
https://www.ncbi.nlm.nih.gov/pubmed/25025525
http://dx.doi.org/10.1021/ol501327g
work_keys_str_mv AT bradypatrickb stereodivergentapproachtotheavermectinsbasedonsupersilyldirectedaldolreactions
AT odasusumu stereodivergentapproachtotheavermectinsbasedonsupersilyldirectedaldolreactions
AT yamamotohisashi stereodivergentapproachtotheavermectinsbasedonsupersilyldirectedaldolreactions

Ejemplares similares