A Biomimetic Strategy to Access the Silybins: Total Synthesis of (-)-Isosilybin A

Benjamin R. McDonald; Antoinette E. Nibbs; Karl A. Scheidt

doi:10.1021/ol503303w

A Biomimetic Strategy to Access the Silybins: Total Synthesis of (-)-Isosilybin A

Benjamin R. McDonald, Antoinette E. Nibbs, Karl A. Scheidt^*

^*Corresponding author for this work

Chemistry

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

23 Scopus citations

Abstract

(Figure Presented). We report the first asymmetric, total synthesis of (-)-isosilybin A. A late-stage catalytic biomimetic cyclization of a highly functionalized chalcone is employed to form the characteristic benzopyranone ring. A robust and flexible approach to this chalcone provides an entry to the preparation of the entire isomeric family of silybin natural products.

Original language	English (US)
Pages (from-to)	98-101
Number of pages	4
Journal	Organic Letters
Volume	17
Issue number	1
DOIs	https://doi.org/10.1021/ol503303w
State	Published - Jan 2 2015

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol503303w

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title = "A Biomimetic Strategy to Access the Silybins: Total Synthesis of (-)-Isosilybin A",

abstract = "(Figure Presented). We report the first asymmetric, total synthesis of (-)-isosilybin A. A late-stage catalytic biomimetic cyclization of a highly functionalized chalcone is employed to form the characteristic benzopyranone ring. A robust and flexible approach to this chalcone provides an entry to the preparation of the entire isomeric family of silybin natural products.",

author = "McDonald, {Benjamin R.} and Nibbs, {Antoinette E.} and Scheidt, {Karl A.}",

note = "Publisher Copyright: {\textcopyright} 2014 American Chemical Society.",

year = "2015",

month = jan,

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doi = "10.1021/ol503303w",

language = "English (US)",

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journal = "Organic Letters",

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T1 - A Biomimetic Strategy to Access the Silybins

T2 - Total Synthesis of (-)-Isosilybin A

AU - McDonald, Benjamin R.

AU - Nibbs, Antoinette E.

AU - Scheidt, Karl A.

PY - 2015/1/2

Y1 - 2015/1/2

N2 - (Figure Presented). We report the first asymmetric, total synthesis of (-)-isosilybin A. A late-stage catalytic biomimetic cyclization of a highly functionalized chalcone is employed to form the characteristic benzopyranone ring. A robust and flexible approach to this chalcone provides an entry to the preparation of the entire isomeric family of silybin natural products.

AB - (Figure Presented). We report the first asymmetric, total synthesis of (-)-isosilybin A. A late-stage catalytic biomimetic cyclization of a highly functionalized chalcone is employed to form the characteristic benzopyranone ring. A robust and flexible approach to this chalcone provides an entry to the preparation of the entire isomeric family of silybin natural products.

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JO - Organic Letters

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A Biomimetic Strategy to Access the Silybins: Total Synthesis of (-)-Isosilybin A

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CCDC 1024173: Experimental Crystal Structure Determination

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A Biomimetic Strategy to Access the Silybins: Total Synthesis of (-)-Isosilybin A

Abstract

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CCDC 1024173: Experimental Crystal Structure Determination

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