O,O-Silyl Group Migrations in Quinic Acid Derivatives: An Opportunity for Divergent Synthesis

Suvi Holmstedt; Alexander Efimov; Nuno R. Candeias

doi:10.1021/acs.orglett.1c00755

O,O-Silyl Group Migrations in Quinic Acid Derivatives: An Opportunity for Divergent Synthesis

Suvi Holmstedt, Alexander Efimov, Nuno R. Candeias

Materiaalitiede ja ympäristötekniikka

Tutkimustuotos: Kirje › Tieteellinen › vertaisarvioitu

4 Sitaatiot (Scopus)

89 Lataukset (Pure)

Abstrakti

The O,O-silyl group migrations on a quinic acid-derived cyclitol have been studied, and the ease of migration was observed to be dependent on the silicon substituents and reaction conditions. Conditions were found to improve the formation of a main isomer during the O,O-silyl group migrations that could be integrated into the formal synthesis of vitamin D receptor modulator VS-105 and in the first total synthesis of a metabolite from the African ant Crematogaster nigriceps.

Alkuperäiskieli	Englanti
Sivut	3083-3087
Sivumäärä	5
Julkaisu	Organic Letters
Vuosikerta	23
Numero	8
DOI - pysyväislinkit	https://doi.org/10.1021/acs.orglett.1c00755
Tila	Julkaistu - 2021
OKM-julkaisutyyppi	A1 Alkuperäisartikkeli tieteellisessä aikakauslehdessä

Rahoitus

The Academy of Finland (Decisions 326487, 326486, and 326416) and Fundação para a Ciência e Tecnologia (PTDC/QUI-QOR/1131/2020 and CEE-CINST/2018) are acknowledged for financial support. The Finnish Cultural Foundation (00190336) is acknowledged for a grant to S.H.

Julkaisufoorumi-taso

Jufo-taso 2

!!ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

Pääsy asiakirjaan

10.1021/acs.orglett.1c00755

Org Lett_noEN
This publication is copyrighted. You may download, display and print it for Your own personal use. Commercial use is prohibited.
Accepted author manuscript, 913 KBLisenssi: Unspecified

https://urn.fi/URN:NBN:fi:tuni-202110157608

Siteeraa tätä

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title = "O,O-Silyl Group Migrations in Quinic Acid Derivatives: An Opportunity for Divergent Synthesis",

abstract = "The O,O-silyl group migrations on a quinic acid-derived cyclitol have been studied, and the ease of migration was observed to be dependent on the silicon substituents and reaction conditions. Conditions were found to improve the formation of a main isomer during the O,O-silyl group migrations that could be integrated into the formal synthesis of vitamin D receptor modulator VS-105 and in the first total synthesis of a metabolite from the African ant Crematogaster nigriceps. ",

author = "Suvi Holmstedt and Alexander Efimov and Candeias, {Nuno R.}",

note = "Funding Information: The Academy of Finland (Decisions 326487, 326486, and 326416) and Funda{\c c}{\~a}o para a Ci{\^e}ncia e Tecnologia (PTDC/QUI-QOR/1131/2020 and CEE-CINST/2018) are acknowledged for financial support. The Finnish Cultural Foundation (00190336) is acknowledged for a grant to S.H. Publisher Copyright: {\textcopyright} 2021 American Chemical Society.",

year = "2021",

doi = "10.1021/acs.orglett.1c00755",

language = "English",

volume = "23",

pages = "3083--3087",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

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TY - JOUR

T1 - O,O-Silyl Group Migrations in Quinic Acid Derivatives

T2 - An Opportunity for Divergent Synthesis

AU - Holmstedt, Suvi

AU - Efimov, Alexander

AU - Candeias, Nuno R.

N1 - Funding Information: The Academy of Finland (Decisions 326487, 326486, and 326416) and Fundação para a Ciência e Tecnologia (PTDC/QUI-QOR/1131/2020 and CEE-CINST/2018) are acknowledged for financial support. The Finnish Cultural Foundation (00190336) is acknowledged for a grant to S.H. Publisher Copyright: © 2021 American Chemical Society.

PY - 2021

Y1 - 2021

N2 - The O,O-silyl group migrations on a quinic acid-derived cyclitol have been studied, and the ease of migration was observed to be dependent on the silicon substituents and reaction conditions. Conditions were found to improve the formation of a main isomer during the O,O-silyl group migrations that could be integrated into the formal synthesis of vitamin D receptor modulator VS-105 and in the first total synthesis of a metabolite from the African ant Crematogaster nigriceps.

AB - The O,O-silyl group migrations on a quinic acid-derived cyclitol have been studied, and the ease of migration was observed to be dependent on the silicon substituents and reaction conditions. Conditions were found to improve the formation of a main isomer during the O,O-silyl group migrations that could be integrated into the formal synthesis of vitamin D receptor modulator VS-105 and in the first total synthesis of a metabolite from the African ant Crematogaster nigriceps.

U2 - 10.1021/acs.orglett.1c00755

DO - 10.1021/acs.orglett.1c00755

M3 - Letter

C2 - 33826343

AN - SCOPUS:85104899760

SN - 1523-7060

VL - 23

SP - 3083

EP - 3087

JO - Organic Letters

JF - Organic Letters

IS - 8

ER -

O,O-Silyl Group Migrations in Quinic Acid Derivatives: An Opportunity for Divergent Synthesis

Abstrakti

Rahoitus

Julkaisufoorumi-taso

!!ASJC Scopus subject areas

Pääsy asiakirjaan

Sormenjälki

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