Total Synthesis of Tagetitoxin

The intriguing structure of tagetitoxin (1), a long-standing challenge in natural product synthesis, has been the subject of multiple revisions and has been confirmed through total synthesis. The route commences from a renewable furan starting material and features a number of unusual transformation...

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Bibliographic Details
Published inJournal of the American Chemical Society Vol. 142; no. 32; pp. 13683 - 13688
Main Authors He, Chi, Chu, Hang, Stratton, Thomas P, Kossler, David, Eberle, Kelly J, Flood, Dillon T, Baran, Phil S
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 12.08.2020
Amer Chemical Soc
Subjects
bioassays
Chemistry
Chemistry, Multidisciplinary
Dicarboxylic Acids - chemical synthesis
Dicarboxylic Acids - chemistry
enantiomers
furans
Molecular Structure
Organophosphorus Compounds - chemical synthesis
Organophosphorus Compounds - chemistry
phosphates
Physical Sciences
Science & Technology
Stereoisomerism
REARRANGEMENT
CORE
OXATHIAPHOSPHOLANE APPROACH
CONVERSION
AMINO
TRANSCRIPTION
SINGLET OXYGEN
DERIVATIVES
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Summary:The intriguing structure of tagetitoxin (1), a long-standing challenge in natural product synthesis, has been the subject of multiple revisions and has been confirmed through total synthesis. The route commences from a renewable furan starting material and features a number of unusual transformations (such as rearrangements, bromocyclization, and P­(V)-based phosphate installation) to arrive at the target in 15 steps. As the route was designed to enable access to both enantiomers, the absolute configuration of the natural product could be assigned using a bioassay on (+)-1 and (−)-1.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:0002-7863
1520-5126
1520-5126
DOI:10.1021/jacs.0c06641