A six-step synthetic approach to marine natural product (+)-aureol

Jun Li Wang; Hui Jing Li; Meirong Wang; Jun Hu Wang; Yan Chao Wu

doi:10.1016/j.tetlet.2018.01.091

A six-step synthetic approach to marine natural product (+)-aureol

Jun Li Wang
, Hui Jing Li
, Meirong Wang
, Jun Hu Wang
, Yan Chao Wu^*

^*Corresponding author for this work

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

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

11 Scopus citations

Abstract

A concise synthetic approach to the marine natural product (+)-aureol has been achieved from readily available starting materials using obviously fewer steps in comparison to the related report in literature (6 steps versus 12 steps from (+)-sclareolide). Key steps of this protocol include a boron trifluoride-catalyzed domino 1,2-H and 1,2-methyl shifts and a nickel(II)-catalyzed cross-coupling reaction between an alkyl iodide and an aryl Grignard reagent.

Original language	English
Pages (from-to)	945-948
Number of pages	4
Journal	Tetrahedron Letters
Volume	59
Issue number	10
DOIs	https://doi.org/10.1016/j.tetlet.2018.01.091
State	Published - 7 Mar 2018
Externally published	Yes

UN SDGs

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

SDG 14 Life Below Water

Keywords

Aureol
Coupling reaction
Marine natural products
Rearrangement

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10.1016/j.tetlet.2018.01.091

Cite this

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title = "A six-step synthetic approach to marine natural product (+)-aureol",

abstract = "A concise synthetic approach to the marine natural product (+)-aureol has been achieved from readily available starting materials using obviously fewer steps in comparison to the related report in literature (6 steps versus 12 steps from (+)-sclareolide). Key steps of this protocol include a boron trifluoride-catalyzed domino 1,2-H and 1,2-methyl shifts and a nickel(II)-catalyzed cross-coupling reaction between an alkyl iodide and an aryl Grignard reagent.",

keywords = "Aureol, Coupling reaction, Marine natural products, Rearrangement",

author = "Wang, \{Jun Li\} and Li, \{Hui Jing\} and Meirong Wang and Wang, \{Jun Hu\} and Wu, \{Yan Chao\}",

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year = "2018",

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doi = "10.1016/j.tetlet.2018.01.091",

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T1 - A six-step synthetic approach to marine natural product (+)-aureol

AU - Wang, Jun Li

AU - Li, Hui Jing

AU - Wang, Meirong

AU - Wang, Jun Hu

AU - Wu, Yan Chao

PY - 2018/3/7

Y1 - 2018/3/7

N2 - A concise synthetic approach to the marine natural product (+)-aureol has been achieved from readily available starting materials using obviously fewer steps in comparison to the related report in literature (6 steps versus 12 steps from (+)-sclareolide). Key steps of this protocol include a boron trifluoride-catalyzed domino 1,2-H and 1,2-methyl shifts and a nickel(II)-catalyzed cross-coupling reaction between an alkyl iodide and an aryl Grignard reagent.

AB - A concise synthetic approach to the marine natural product (+)-aureol has been achieved from readily available starting materials using obviously fewer steps in comparison to the related report in literature (6 steps versus 12 steps from (+)-sclareolide). Key steps of this protocol include a boron trifluoride-catalyzed domino 1,2-H and 1,2-methyl shifts and a nickel(II)-catalyzed cross-coupling reaction between an alkyl iodide and an aryl Grignard reagent.

KW - Aureol

KW - Coupling reaction

KW - Marine natural products

KW - Rearrangement

UR - https://www.scopus.com/pages/publications/85041518790

U2 - 10.1016/j.tetlet.2018.01.091

DO - 10.1016/j.tetlet.2018.01.091

M3 - 文章

AN - SCOPUS:85041518790

SN - 0040-4039

VL - 59

SP - 945

EP - 948

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 10

ER -

A six-step synthetic approach to marine natural product (+)-aureol

Abstract

UN SDGs

Keywords

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