Total Synthesis of (–)-Sessilifoliamide C and (–)-8-epi-Stemoamide

A convergent route featuring [3,3]-sigmatropic rearrangements of a linchpin azepinopyrrolidine served to install two of the four contiguous stereocenters present in the tricyclic Stemona alkaloids sessilifoliamide and stemoamide. In addition to the first total synthesis of (–)-sessilifoliamide C, a...

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Bibliographic Details
Published inOrganic letters Vol. 13; no. 10; pp. 2634 - 2637
Main Authors Hoye, Adam T, Wipf, Peter
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 20.05.2011
Amer Chemical Soc
Subjects
Alkaloids - chemical synthesis
Alkaloids - chemistry
Chemistry
Chemistry, Organic
Heterocyclic Compounds, 3-Ring - chemical synthesis
Heterocyclic Compounds, 3-Ring - chemistry
Molecular Structure
Physical Sciences
Science & Technology
Stemonaceae - chemistry
Stereoisomerism
ENOLATE CLAISEN REARRANGEMENT
ASYMMETRIC-SYNTHESIS
(-)-STEMOAMIDE
STEREOSELECTIVITY
STEREOCHEMICAL CONTROL
CHIRAL POOL
ENYNE METATHESIS REACTION
RING-SYSTEM
ENANTIOSELECTIVE TOTAL-SYNTHESIS
STEMONA ALKALOIDS
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Summary:A convergent route featuring [3,3]-sigmatropic rearrangements of a linchpin azepinopyrrolidine served to install two of the four contiguous stereocenters present in the tricyclic Stemona alkaloids sessilifoliamide and stemoamide. In addition to the first total synthesis of (–)-sessilifoliamide C, a potential biosynthetic relationship between the sessilifoliamides and previously reported Stemona alkaloids is presented.
Bibliography:NIH RePORTER
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol200743u