Formal total synthesis of selaginpulvilin D

An efficient and mild synthetic strategy for the total synthesis of selaginpulvilin D has been reported. A highly chemoselective enyne-alkyne dehydro Diels-Alder reaction has been employed for the construction of the tricyclic fluorene framework present in the natural product selaginpulvilin D. An i...

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Bibliographic Details
Published inOrganic & biomolecular chemistry Vol. 15; no. 28; pp. 5908 - 5911
Main Authors Chinta, Bhavani Shankar, Baire, Beeraiah
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 2017
Subjects
Alkynes - chemical synthesis
Alkynes - chemistry
Biological Products - chemical synthesis
Biological Products - chemistry
Chemistry
Chemistry, Organic
Cycloaddition Reaction
Molecular Structure
Physical Sciences
Polycyclic Compounds - chemical synthesis
Polycyclic Compounds - chemistry
Science & Technology
Stereoisomerism
CONJUGATED ENYNES
DERIVATIVES
FIELD
DIELS-ALDER REACTION
4+2 CYCLOADDITION REACTIONS
CYCLOAROMATIZATION
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Summary:An efficient and mild synthetic strategy for the total synthesis of selaginpulvilin D has been reported. A highly chemoselective enyne-alkyne dehydro Diels-Alder reaction has been employed for the construction of the tricyclic fluorene framework present in the natural product selaginpulvilin D. An improved overall yield (10.5%) has been achieved for selaginpulvilin D, starting from commercially available m-anisaldehyde in 9 linear, operationally simple synthetic transformations.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:1477-0520
1477-0539
DOI:10.1039/c7ob00950j