C-H functionalization logic enables synthesis of (+)-hongoquercin A and related compounds

Brandon R. Rosen; Leah R. Simke; Peter S. Thuy-Boun; Darryl D. Dixon; Jin Quan Yu; Phil S. Baran

doi:10.1002/anie.201303838

C-H functionalization logic enables synthesis of (+)-hongoquercin A and related compounds

Brandon R. Rosen
, Leah R. Simke
, Peter S. Thuy-Boun
, Darryl D. Dixon
, Jin Quan Yu
, Phil S. Baran

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

152 Scopus citations

Abstract

The specifics: A synthesis of the sesquiterpenoid antibiotic (+)-hongoquercin A using sequential site-specific C-H methylation and oxidation reactions is described. A key advancement toward this goal was the development of a ligand-accelerated C-H methylation reaction, and enabled the generation of a library of eight structurally diverse analogues.

Original language	English
Pages (from-to)	7317-7320
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	52
Issue number	28
DOIs	https://doi.org/10.1002/anie.201303838
State	Published - 8 Jul 2013
Externally published	Yes

Keywords

C-H functionalization
natural products
oxidation
synthesis design
synthetic methods

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10.1002/anie.201303838

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title = "C-H functionalization logic enables synthesis of (+)-hongoquercin A and related compounds",

abstract = "The specifics: A synthesis of the sesquiterpenoid antibiotic (+)-hongoquercin A using sequential site-specific C-H methylation and oxidation reactions is described. A key advancement toward this goal was the development of a ligand-accelerated C-H methylation reaction, and enabled the generation of a library of eight structurally diverse analogues.",

keywords = "C-H functionalization, natural products, oxidation, synthesis design, synthetic methods",

author = "Rosen, \{Brandon R.\} and Simke, \{Leah R.\} and Thuy-Boun, \{Peter S.\} and Dixon, \{Darryl D.\} and Yu, \{Jin Quan\} and Baran, \{Phil S.\}",

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AU - Simke, Leah R.

AU - Thuy-Boun, Peter S.

AU - Dixon, Darryl D.

AU - Yu, Jin Quan

AU - Baran, Phil S.

PY - 2013/7/8

Y1 - 2013/7/8

N2 - The specifics: A synthesis of the sesquiterpenoid antibiotic (+)-hongoquercin A using sequential site-specific C-H methylation and oxidation reactions is described. A key advancement toward this goal was the development of a ligand-accelerated C-H methylation reaction, and enabled the generation of a library of eight structurally diverse analogues.

AB - The specifics: A synthesis of the sesquiterpenoid antibiotic (+)-hongoquercin A using sequential site-specific C-H methylation and oxidation reactions is described. A key advancement toward this goal was the development of a ligand-accelerated C-H methylation reaction, and enabled the generation of a library of eight structurally diverse analogues.

KW - C-H functionalization

KW - natural products

KW - oxidation

KW - synthesis design

KW - synthetic methods

UR - https://www.scopus.com/pages/publications/84880146997

U2 - 10.1002/anie.201303838

DO - 10.1002/anie.201303838

M3 - Article

C2 - 23740529

AN - SCOPUS:84880146997

SN - 1433-7851

VL - 52

SP - 7317

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JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 28

ER -

C-H functionalization logic enables synthesis of (+)-hongoquercin A and related compounds

Abstract

Keywords

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