Total Synthesis of (+)-Superstolide A

A convergent and highly stereocontrolled synthesis of (+)-superstolide A (1) has been accomplished. Key steps of this synthesis include the intramolecular Suzuki reaction of 26 and the highly diastereoselective transannular Diels−Alder cyclization of macrocyclic octaene 3.

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Bibliographic Details
Published inJournal of the American Chemical Society Vol. 130; no. 9; pp. 2722 - 2723
Main Authors Tortosa, Mariola, Yakelis, Neal A, Roush, William R
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 05.03.2008
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Multidisciplinary
Cyclization
Cytotoxins - chemical synthesis
Cytotoxins - chemistry
Macrolides - chemical synthesis
Macrolides - chemistry
Molecular Conformation
Physical Sciences
Science & Technology
Stereoisomerism
Tetrahydronaphthalenes - chemical synthesis
Tetrahydronaphthalenes - chemistry
REAGENT
OXIDATION
ALCOHOLS
C-C FRAGMENT
NATURAL-PRODUCTS
DIELS-ALDER REACTION
CONSTRUCTION
CYTOTOXIC MACROLIDE
STEREOSELECTIVE-SYNTHESIS
SUPERSTOLIDE-A
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Summary:A convergent and highly stereocontrolled synthesis of (+)-superstolide A (1) has been accomplished. Key steps of this synthesis include the intramolecular Suzuki reaction of 26 and the highly diastereoselective transannular Diels−Alder cyclization of macrocyclic octaene 3.
Bibliography:ark:/67375/TPS-5NQ8T56V-H
istex:F3E0AD7FBB0739C0FAE00DA4E86120049C268D0E
Medline
NIH RePORTER
ISSN:0002-7863
1520-5126
DOI:10.1021/ja710238h