Divergent Synthesis of Bioactive Marine Meroterpenoids by Palladium-Catalyzed Tandem Carbene Migratory Insertion

Hong Shuang Wang; Hui Jing Li; Zhen Guo Zhang; Yan Chao Wu

doi:10.1002/ejoc.201800026

Divergent Synthesis of Bioactive Marine Meroterpenoids by Palladium-Catalyzed Tandem Carbene Migratory Insertion

Hong Shuang Wang
, Hui Jing Li^*
, Zhen Guo Zhang
, Yan Chao Wu

^*Corresponding author for this work

School of Marine Science and Technology, Harbin Institute of Technology Weihai
Peking University

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

30 Scopus citations

Abstract

The divergent synthesis of (+)-8-epi-puupehedione, (+)-chromazonarol, (+)-yahazunol, and (+)-yahazunone has been accomplished. The key steps were a palladium-catalyzed tandem carbene migratory insertion of an aryl iodide and a drimanal hydrazone, a highly regioselective enol reduction, an oxa-Stork–Danheiser transposition reaction, an electrocyclization of a conjugated tetraenone, and a redox reaction of dimethoxybenzenes.

Original language	English
Pages (from-to)	915-925
Number of pages	11
Journal	European Journal of Organic Chemistry
Volume	2018
Issue number	7
DOIs	https://doi.org/10.1002/ejoc.201800026
State	Published - 21 Feb 2018
Externally published	Yes

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

SDG 14 Life Below Water

Keywords

Chiral pool
Meroterpenoids
Natural products
Synthesis design
Terpenoids
Total synthesis

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10.1002/ejoc.201800026

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title = "Divergent Synthesis of Bioactive Marine Meroterpenoids by Palladium-Catalyzed Tandem Carbene Migratory Insertion",

abstract = "The divergent synthesis of (+)-8-epi-puupehedione, (+)-chromazonarol, (+)-yahazunol, and (+)-yahazunone has been accomplished. The key steps were a palladium-catalyzed tandem carbene migratory insertion of an aryl iodide and a drimanal hydrazone, a highly regioselective enol reduction, an oxa-Stork–Danheiser transposition reaction, an electrocyclization of a conjugated tetraenone, and a redox reaction of dimethoxybenzenes.",

keywords = "Chiral pool, Meroterpenoids, Natural products, Synthesis design, Terpenoids, Total synthesis",

author = "Wang, \{Hong Shuang\} and Li, \{Hui Jing\} and Zhang, \{Zhen Guo\} and Wu, \{Yan Chao\}",

note = "Publisher Copyright: {\textcopyright} 2018 WILEY-VCH Verlag GmbH \& Co. KGaA, Weinheim",

year = "2018",

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doi = "10.1002/ejoc.201800026",

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journal = "European Journal of Organic Chemistry",

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T1 - Divergent Synthesis of Bioactive Marine Meroterpenoids by Palladium-Catalyzed Tandem Carbene Migratory Insertion

AU - Wang, Hong Shuang

AU - Li, Hui Jing

AU - Zhang, Zhen Guo

AU - Wu, Yan Chao

PY - 2018/2/21

Y1 - 2018/2/21

N2 - The divergent synthesis of (+)-8-epi-puupehedione, (+)-chromazonarol, (+)-yahazunol, and (+)-yahazunone has been accomplished. The key steps were a palladium-catalyzed tandem carbene migratory insertion of an aryl iodide and a drimanal hydrazone, a highly regioselective enol reduction, an oxa-Stork–Danheiser transposition reaction, an electrocyclization of a conjugated tetraenone, and a redox reaction of dimethoxybenzenes.

AB - The divergent synthesis of (+)-8-epi-puupehedione, (+)-chromazonarol, (+)-yahazunol, and (+)-yahazunone has been accomplished. The key steps were a palladium-catalyzed tandem carbene migratory insertion of an aryl iodide and a drimanal hydrazone, a highly regioselective enol reduction, an oxa-Stork–Danheiser transposition reaction, an electrocyclization of a conjugated tetraenone, and a redox reaction of dimethoxybenzenes.

KW - Chiral pool

KW - Meroterpenoids

KW - Natural products

KW - Synthesis design

KW - Terpenoids

KW - Total synthesis

UR - https://www.scopus.com/pages/publications/85042304836

U2 - 10.1002/ejoc.201800026

DO - 10.1002/ejoc.201800026

M3 - 文章

AN - SCOPUS:85042304836

SN - 1434-193X

VL - 2018

SP - 915

EP - 925

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 7

ER -

Divergent Synthesis of Bioactive Marine Meroterpenoids by Palladium-Catalyzed Tandem Carbene Migratory Insertion

Abstract

UN SDGs

Keywords

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