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

17 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

Access to Document

10.1021/ol503303w

Fingerprint Dive into the research topics of 'A Biomimetic Strategy to Access the Silybins: Total Synthesis of (-)-Isosilybin A'. Together they form a unique fingerprint.

Cite this

@article{cb2d33f0829543dea49e6eee0bf8abe5,

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.}",

year = "2015",

month = jan,

day = "2",

doi = "10.1021/ol503303w",

language = "English (US)",

volume = "17",

pages = "98--101",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "1",

}

TY - JOUR

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.

UR - http://www.scopus.com/inward/record.url?scp=84928319738&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84928319738&partnerID=8YFLogxK

U2 - 10.1021/ol503303w

DO - 10.1021/ol503303w

M3 - Article

C2 - 25517432

AN - SCOPUS:84928319738

VL - 17

SP - 98

EP - 101

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 1

ER -