Stereoselective β-C-glycosylation by a palladium-catalyzed decarboxylative allylation : formal synthesis of aspergillide A

Stereoselective β-C-glycosylation by a palladium-catalyzed decarboxylative allylation : formal synthesis of aspergillide A

Mild and sweet: The title reaction proceeds under mild conditions with high regio- and diastereoselectivity (see scheme, PG=protecting group, DiPPF=1,1′-bis(diisopropylphosphino)ferrocene). This reaction is suitable for a wide range of glycal-derived γ-ketone esters and affords C-glycosides with exc...

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Main Authors: Xiang, Shaohua, Cai, Shuting, Liu, Xue-Wei, Zeng, Jing, Ma, Jimei
Other Authors: School of Physical and Mathematical Sciences
Format: Article
Language:English
Published: 2014
Subjects:
DRNTU::Science::Chemistry::Organic chemistry::Organometallic compounds
Online Access:https://hdl.handle.net/10356/102577
http://hdl.handle.net/10220/19122
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Institution: Nanyang Technological University
Language: English
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spelling sg-ntu-dr.10356-1025772020-03-07T12:34:52Z Stereoselective β-C-glycosylation by a palladium-catalyzed decarboxylative allylation : formal synthesis of aspergillide A Xiang, Shaohua Cai, Shuting Liu, Xue-Wei Zeng, Jing Ma, Jimei School of Physical and Mathematical Sciences DRNTU::Science::Chemistry::Organic chemistry::Organometallic compounds Mild and sweet: The title reaction proceeds under mild conditions with high regio- and diastereoselectivity (see scheme, PG=protecting group, DiPPF=1,1′-bis(diisopropylphosphino)ferrocene). This reaction is suitable for a wide range of glycal-derived γ-ketone esters and affords C-glycosides with exclusive β-selectivity. The method was further applied to a concise formal synthesis of aspergillide A. 2014-04-04T07:32:42Z 2019-12-06T20:57:06Z 2014-04-04T07:32:42Z 2019-12-06T20:57:06Z 2013 2013 Journal Article Zeng, J., Ma, J., Xiang, S., Cai, S., & Liu, X.-W. (2013). Stereoselective β-C-glycosylation by a palladium-catalyzed decarboxylative allylation : formal synthesis of aspergillide A. Angewandte Chemie International Edition, 52(19), 5134-5137. 1433-7851 https://hdl.handle.net/10356/102577 http://hdl.handle.net/10220/19122 10.1002/anie.201210266 en Angewandte chemie international edition © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
institution Nanyang Technological University
building NTU Library
country Singapore
collection DR-NTU
language English
topic DRNTU::Science::Chemistry::Organic chemistry::Organometallic compounds
spellingShingle DRNTU::Science::Chemistry::Organic chemistry::Organometallic compounds
Xiang, Shaohua
Cai, Shuting
Liu, Xue-Wei
Zeng, Jing
Ma, Jimei
Stereoselective β-C-glycosylation by a palladium-catalyzed decarboxylative allylation : formal synthesis of aspergillide A
description Mild and sweet: The title reaction proceeds under mild conditions with high regio- and diastereoselectivity (see scheme, PG=protecting group, DiPPF=1,1′-bis(diisopropylphosphino)ferrocene). This reaction is suitable for a wide range of glycal-derived γ-ketone esters and affords C-glycosides with exclusive β-selectivity. The method was further applied to a concise formal synthesis of aspergillide A.
author2 School of Physical and Mathematical Sciences
author_facet School of Physical and Mathematical Sciences
Xiang, Shaohua
Cai, Shuting
Liu, Xue-Wei
Zeng, Jing
Ma, Jimei
format Article
author Xiang, Shaohua
Cai, Shuting
Liu, Xue-Wei
Zeng, Jing
Ma, Jimei
author_sort Xiang, Shaohua
title Stereoselective β-C-glycosylation by a palladium-catalyzed decarboxylative allylation : formal synthesis of aspergillide A
title_short Stereoselective β-C-glycosylation by a palladium-catalyzed decarboxylative allylation : formal synthesis of aspergillide A
title_full Stereoselective β-C-glycosylation by a palladium-catalyzed decarboxylative allylation : formal synthesis of aspergillide A
title_fullStr Stereoselective β-C-glycosylation by a palladium-catalyzed decarboxylative allylation : formal synthesis of aspergillide A
title_full_unstemmed Stereoselective β-C-glycosylation by a palladium-catalyzed decarboxylative allylation : formal synthesis of aspergillide A
title_sort stereoselective β-c-glycosylation by a palladium-catalyzed decarboxylative allylation : formal synthesis of aspergillide a
publishDate 2014
url https://hdl.handle.net/10356/102577
http://hdl.handle.net/10220/19122
_version_ 1681045075407142912

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