Total Synthesis of Isohericerin, Isohericenone, and Erinacerin A: Development of a Copper-Catalyzed Methylboronation of Terminal Alkynes

Efficient and concise approaches for the synthesis of three bioactive natural products, isohericerin, isohericenone, and erinacerin A, are described in this paper. The key reactions employed include a Mannich reaction with commercially available hydroxy­benzoate and subsequent one-pot lactamization...

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Bibliographic Details
Published inJournal of organic chemistry Vol. 82; no. 12; pp. 6349 - 6357
Main Authors Mun, Bohyun, Kim, Sangyong, Yoon, Hongju, Kim, Ki Hyun, Lee, Yunmi
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 16.06.2017
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
MUSHROOM
ALLYLIC ALCOHOLS
HERICIUM-ERINACEUM
NATURAL-PRODUCTS
DEHYDROGENATIVE BORYLATION
CARBOBORATION
ALLYLATION
STEREOSELECTIVE-SYNTHESIS
LIGAND
AROMATIC-COMPOUNDS
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Summary:Efficient and concise approaches for the synthesis of three bioactive natural products, isohericerin, isohericenone, and erinacerin A, are described in this paper. The key reactions employed include a Mannich reaction with commercially available hydroxy­benzoate and subsequent one-pot lactamization to afford the common precursor isoindolinone in 3 steps and a Suzuki–Miyaura coupling reaction to connect geranyl side chains to the isoindolinone core. In addition, the mild and efficient synthesis of the C5′-oxidized geranyl side unit of isohericenone is enabled by developing a highly regioselective and efficient method for the Cu-catalyzed methylboronation of functionalized terminal alkynes.
Bibliography:ObjectType-Article-1
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ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.7b00920