Synthesis of the Right‐Side Structure of Type B Physalins

We present a full account of our synthetic studies on the racemic DEFGH‐ring moiety of physalins, featuring domino ring transformation of a tricyclic key intermediate. We also report the results of a detailed mechanistic examination of the domino ring transformation, as well as a reoptimization of t...

Descripción completa

Detalles Bibliográficos
Autores principales: Morita, Masaki, Kojima, Shuntaro, Ohkubo, Megumi, Koshino, Hiroyuki, Hashizume, Daisuke, Hirai, Go, Maruoka, Keiji, Sodeoka, Mikiko
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2016
Materias:
Full Papers
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5467525/
https://www.ncbi.nlm.nih.gov/pubmed/28659646
http://dx.doi.org/10.1002/ijch.201600110
_version_ 1783243283881787392
author Morita, Masaki
Kojima, Shuntaro
Ohkubo, Megumi
Koshino, Hiroyuki
Hashizume, Daisuke
Hirai, Go
Maruoka, Keiji
Sodeoka, Mikiko
author_facet Morita, Masaki
Kojima, Shuntaro
Ohkubo, Megumi
Koshino, Hiroyuki
Hashizume, Daisuke
Hirai, Go
Maruoka, Keiji
Sodeoka, Mikiko
author_sort Morita, Masaki
collection PubMed
description We present a full account of our synthetic studies on the racemic DEFGH‐ring moiety of physalins, featuring domino ring transformation of a tricyclic key intermediate. We also report the results of a detailed mechanistic examination of the domino ring transformation, as well as a reoptimization of the 2,3‐Wittig rearrangement and methylation steps. Furthermore, we have newly established a method for the preparation of an optically active synthetic intermediate by enzymatic kinetic resolution. Our work provides access to both natural and nonnatural right‐side physalin structures.
format Online
Article
Text
id pubmed-5467525
institution National Center for Biotechnology Information
language English
publishDate 2016
publisher John Wiley and Sons Inc.
record_format MEDLINE/PubMed
spelling pubmed-54675252017-06-26 Synthesis of the Right‐Side Structure of Type B Physalins Morita, Masaki Kojima, Shuntaro Ohkubo, Megumi Koshino, Hiroyuki Hashizume, Daisuke Hirai, Go Maruoka, Keiji Sodeoka, Mikiko Isr J Chem Full Papers We present a full account of our synthetic studies on the racemic DEFGH‐ring moiety of physalins, featuring domino ring transformation of a tricyclic key intermediate. We also report the results of a detailed mechanistic examination of the domino ring transformation, as well as a reoptimization of the 2,3‐Wittig rearrangement and methylation steps. Furthermore, we have newly established a method for the preparation of an optically active synthetic intermediate by enzymatic kinetic resolution. Our work provides access to both natural and nonnatural right‐side physalin structures. John Wiley and Sons Inc. 2016-11-09 2017-04 /pmc/articles/PMC5467525/ /pubmed/28659646 http://dx.doi.org/10.1002/ijch.201600110 Text en © 2016 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution‐NonCommercial‐NoDerivs (http://creativecommons.org/licenses/by-nc-nd/4.0/) License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non‐commercial and no modifications or adaptations are made.
spellingShingle Full Papers
Morita, Masaki
Kojima, Shuntaro
Ohkubo, Megumi
Koshino, Hiroyuki
Hashizume, Daisuke
Hirai, Go
Maruoka, Keiji
Sodeoka, Mikiko
Synthesis of the Right‐Side Structure of Type B Physalins
title Synthesis of the Right‐Side Structure of Type B Physalins
title_full Synthesis of the Right‐Side Structure of Type B Physalins
title_fullStr Synthesis of the Right‐Side Structure of Type B Physalins
title_full_unstemmed Synthesis of the Right‐Side Structure of Type B Physalins
title_short Synthesis of the Right‐Side Structure of Type B Physalins
title_sort synthesis of the right‐side structure of type b physalins
topic Full Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5467525/
https://www.ncbi.nlm.nih.gov/pubmed/28659646
http://dx.doi.org/10.1002/ijch.201600110
work_keys_str_mv AT moritamasaki synthesisoftherightsidestructureoftypebphysalins
AT kojimashuntaro synthesisoftherightsidestructureoftypebphysalins
AT ohkubomegumi synthesisoftherightsidestructureoftypebphysalins
AT koshinohiroyuki synthesisoftherightsidestructureoftypebphysalins
AT hashizumedaisuke synthesisoftherightsidestructureoftypebphysalins
AT hiraigo synthesisoftherightsidestructureoftypebphysalins
AT maruokakeiji synthesisoftherightsidestructureoftypebphysalins
AT sodeokamikiko synthesisoftherightsidestructureoftypebphysalins

Ejemplares similares