Palladium-Catalyzed Cyclization of Free Hydroxyalkenoic Acids: Regio- and Chemoselective Access to Methylene Lactones

Yelena Mostinski; Ramesh Kotikalapudi; Viviana Valerio; Riva Nataf; Dmitry Tsvelikhovsky

doi:10.1002/adsc.201601346

Palladium-Catalyzed Cyclization of Free Hydroxyalkenoic Acids: Regio- and Chemoselective Access to Methylene Lactones

Yelena Mostinski, Ramesh Kotikalapudi, Viviana Valerio, Riva Nataf, Dmitry Tsvelikhovsky^*

^*Corresponding author for this work

School of Pharmacy

Research output: Contribution to journal › Article › peer-review

3 Scopus citations

Abstract

A general and collective synthesis of medium-sized methylene lactones via controlled cyclizations of easily accessible collective precursors is described. The rapid composition of key–hydroxyalkenoic acid scaffold yields an assembly of oxocanones, oxepanones, and pyranones in a regioselective and stereodirected fashion via palladium-catalyzed cyclization. (Figure presented.).

Original language	English
Pages (from-to)	1164-1169
Number of pages	6
Journal	Advanced Synthesis and Catalysis
Volume	359
Issue number	7
DOIs	https://doi.org/10.1002/adsc.201601346
State	Published - 3 Apr 2017

Bibliographical note

Funding Information:
This project was financially supported by Yissum Research Development Company of the Hebrew University of Jerusalem. V. V. thanks Minerva-Stiftung for a postdoctoral fellowship.

Publisher Copyright:
© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

Keywords

cyclizations
hydroxyalkenoic acids
lactones
palladium
regioselectivity

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10.1002/adsc.201601346

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title = "Palladium-Catalyzed Cyclization of Free Hydroxyalkenoic Acids: Regio- and Chemoselective Access to Methylene Lactones",

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T2 - Regio- and Chemoselective Access to Methylene Lactones

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AU - Kotikalapudi, Ramesh

AU - Valerio, Viviana

AU - Nataf, Riva

AU - Tsvelikhovsky, Dmitry

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AB - A general and collective synthesis of medium-sized methylene lactones via controlled cyclizations of easily accessible collective precursors is described. The rapid composition of key–hydroxyalkenoic acid scaffold yields an assembly of oxocanones, oxepanones, and pyranones in a regioselective and stereodirected fashion via palladium-catalyzed cyclization. (Figure presented.).

KW - cyclizations

KW - hydroxyalkenoic acids

KW - lactones

KW - palladium

KW - regioselectivity

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Palladium-Catalyzed Cyclization of Free Hydroxyalkenoic Acids: Regio- and Chemoselective Access to Methylene Lactones

Abstract

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Keywords

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