Enantioselective total synthesis of ( - )-kibdelone C

John R. Butler, Chao Wang, Jianwei Bian, Joseph M. Ready

Research output: Contribution to journalArticle

47 Citations (Scopus)

Abstract

The kibdelones are aromatic polyketide natural products featuring isoquinolinone and tetrahydroxanthone ring systems. They display potent cytotoxicity toward a range of human cancer cell lines. Here, we present an enantioselective total synthesis of kibdelone C that utilizes a Shi epoxidation to establish the absolute and relative stereochemistry, an acid-catalyzed cyclization to form the tetrahydroxanthone, and a C - H arylation to complete the hexacyclic skeleton.

Original languageEnglish (US)
Pages (from-to)9956-9959
Number of pages4
JournalJournal of the American Chemical Society
Volume133
Issue number26
DOIs
StatePublished - Jul 6 2011

Fingerprint

Polyketides
Stereochemistry
Epoxidation
Cyclization
Cytotoxicity
Biological Products
Skeleton
Cells
Cell Line
Acids
Neoplasms
kibdelone C

ASJC Scopus subject areas

  • Chemistry(all)
  • Catalysis
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

Enantioselective total synthesis of ( - )-kibdelone C. / Butler, John R.; Wang, Chao; Bian, Jianwei; Ready, Joseph M.

In: Journal of the American Chemical Society, Vol. 133, No. 26, 06.07.2011, p. 9956-9959.

Research output: Contribution to journalArticle

Butler, John R. ; Wang, Chao ; Bian, Jianwei ; Ready, Joseph M. / Enantioselective total synthesis of ( - )-kibdelone C. In: Journal of the American Chemical Society. 2011 ; Vol. 133, No. 26. pp. 9956-9959.
@article{fe5bb8128d874157a1157656ee041087,
title = "Enantioselective total synthesis of ( - )-kibdelone C",
abstract = "The kibdelones are aromatic polyketide natural products featuring isoquinolinone and tetrahydroxanthone ring systems. They display potent cytotoxicity toward a range of human cancer cell lines. Here, we present an enantioselective total synthesis of kibdelone C that utilizes a Shi epoxidation to establish the absolute and relative stereochemistry, an acid-catalyzed cyclization to form the tetrahydroxanthone, and a C - H arylation to complete the hexacyclic skeleton.",
author = "Butler, {John R.} and Chao Wang and Jianwei Bian and Ready, {Joseph M.}",
year = "2011",
month = "7",
day = "6",
doi = "10.1021/ja204040k",
language = "English (US)",
volume = "133",
pages = "9956--9959",
journal = "Journal of the American Chemical Society",
issn = "0002-7863",
publisher = "American Chemical Society",
number = "26",

}

TY - JOUR

T1 - Enantioselective total synthesis of ( - )-kibdelone C

AU - Butler, John R.

AU - Wang, Chao

AU - Bian, Jianwei

AU - Ready, Joseph M.

PY - 2011/7/6

Y1 - 2011/7/6

N2 - The kibdelones are aromatic polyketide natural products featuring isoquinolinone and tetrahydroxanthone ring systems. They display potent cytotoxicity toward a range of human cancer cell lines. Here, we present an enantioselective total synthesis of kibdelone C that utilizes a Shi epoxidation to establish the absolute and relative stereochemistry, an acid-catalyzed cyclization to form the tetrahydroxanthone, and a C - H arylation to complete the hexacyclic skeleton.

AB - The kibdelones are aromatic polyketide natural products featuring isoquinolinone and tetrahydroxanthone ring systems. They display potent cytotoxicity toward a range of human cancer cell lines. Here, we present an enantioselective total synthesis of kibdelone C that utilizes a Shi epoxidation to establish the absolute and relative stereochemistry, an acid-catalyzed cyclization to form the tetrahydroxanthone, and a C - H arylation to complete the hexacyclic skeleton.

UR - http://www.scopus.com/inward/record.url?scp=79959863573&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=79959863573&partnerID=8YFLogxK

U2 - 10.1021/ja204040k

DO - 10.1021/ja204040k

M3 - Article

C2 - 21648478

AN - SCOPUS:79959863573

VL - 133

SP - 9956

EP - 9959

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

SN - 0002-7863

IS - 26

ER -