Nature-Inspired Total Synthesis of (−)-Fusarisetin A

A concise, protecting group-free total synthesis of (−)-fusarisetin A (1) was efficiently achieved in nine steps from commercially available (S)-(−)-citronellal. The synthetic approach was inspired by our proposed biosynthesis of 1. Key transformations of our strategy include a facile construction o...

Full description

Saved in:
Bibliographic Details
Published inJournal of the American Chemical Society Vol. 134; no. 11; pp. 5072 - 5075
Main Authors Xu, Jing, Caro-Diaz, Eduardo J. E, Trzoss, Lynnie, Theodorakis, Emmanuel A
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 21.03.2012
Amer Chemical Soc
Subjects
Antineoplastic Agents - chemical synthesis
Antineoplastic Agents - chemistry
Chemistry
Chemistry, Multidisciplinary
Heterocyclic Compounds, 4 or More Rings - chemical synthesis
Heterocyclic Compounds, 4 or More Rings - chemistry
Molecular Conformation
Physical Sciences
Science & Technology
Stereoisomerism
PROTECTING-GROUP-FREE
UNIFIED SYNTHESIS
ENDOPHYTIC FUNGUS
ASYMMETRIC-SYNTHESIS
DIELS-ALDER REACTIONS
ABSOLUTE-CONFIGURATION
FUSARIUM TOXIN EQUISETIN
STEREOSELECTIVE TOTAL-SYNTHESIS
ENANTIOSELECTIVE TOTAL-SYNTHESIS
RADICAL REACTIONS
Online AccessGet full text

Cover

More Information
Summary:A concise, protecting group-free total synthesis of (−)-fusarisetin A (1) was efficiently achieved in nine steps from commercially available (S)-(−)-citronellal. The synthetic approach was inspired by our proposed biosynthesis of 1. Key transformations of our strategy include a facile construction of the decalin moiety that is produced via a stereoselective IMDA reaction and a one-pot TEMPO-induced radical cyclization/aminolysis that forms the C ring of 1. Our route is amenable to analogue synthesis for biological evaluation.
Bibliography:NIH RePORTER
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0002-7863
1520-5126
DOI:10.1021/ja300807e