Enantioselective Total Synthesis of (−)-Kibdelone C

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 est...

Full description

Saved in:
Bibliographic Details
Published inJournal of the American Chemical Society Vol. 133; no. 26; pp. 9956 - 9959
Main Authors Butler, John R, Wang, Chao, Bian, Jianwei, Ready, Joseph M
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 06.07.2011
Amer Chemical Soc
Subjects
Antineoplastic Agents - chemical synthesis
Antineoplastic Agents - chemistry
Cell Line, Tumor
Chemistry
Chemistry Techniques, Synthetic - methods
Chemistry, Multidisciplinary
Humans
Physical Sciences
Science & Technology
Stereoisomerism
Substrate Specificity
Xanthones - chemical synthesis
Xanthones - chemistry
ARYL BROMIDES
ROOM-TEMPERATURE
POTENT
DIRECT ARYLATION
INHIBITION
COMPLEXES
ALPHA
POLYKETIDES
DERIVATIVES
(+/-)-CERVINOMYCIN-A2
Online AccessGet full text

Cover

More Information
Summary: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.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0002-7863
1520-5126
DOI:10.1021/ja204040k