Studies Toward the Enantiospecific Total Synthesis of Rhodexin A

Studies toward the enantiospecific total synthesis of rhodexin A via a very hindered inverse electron demand Diels–Alder reaction are described. The C8-diastereomer of the fully elaborated tetracyclic core of rhodexin A, 23, was prepared in good yield and excellent selectivity using as the key step...

Full description

Saved in:
Bibliographic Details
Published inJournal of organic chemistry Vol. 78; no. 15; pp. 7518 - 7526
Main Authors Jung, Michael E, Guzaev, Mikhail
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 02.08.2013
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Crystallography, X-Ray
Glycosides - chemical synthesis
Glycosides - chemistry
Lactones - chemical synthesis
Lactones - chemistry
Models, Molecular
Molecular Conformation
Physical Sciences
Science & Technology
Stereoisomerism
JAPONICA
TRIMETHYLSILYL IODIDE
REAGENTS
QUANTITATIVE DEALKYLATION
GENERATION
HIF-1-ALPHA
CONJUGATE ADDITIONS
CANCER
DERIVATIVES
CARDIAC-GLYCOSIDES
Online AccessGet full text

Cover

More Information
Summary:Studies toward the enantiospecific total synthesis of rhodexin A via a very hindered inverse electron demand Diels–Alder reaction are described. The C8-diastereomer of the fully elaborated tetracyclic core of rhodexin A, 23, was prepared in good yield and excellent selectivity using as the key step the stepwise Diels–Alder reaction of the very hindered dienone 3 and the silyl enol ether 4 catalyzed by the very strong Lewis acid, dimethylaluminum triflimide.
Bibliography:National Science Foundation
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0022-3263
1520-6904
DOI:10.1021/jo400909t