A Synthesis of Alsmaphorazine B Demonstrates the Chemical Feasibility of a New Biogenetic Hypothesis

An N-oxide fragmentation/hydroxylamine oxidation/intramolecular 1,3-dipolar cycloaddition. Cascade, efficiently converted an oxidized congener of akuammicine into the complex, hexacyclic architecture of the alsmaphorazine alkaloids. This dramatic structural Change shows the chemical feasibility of o...

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Veröffentlicht in:Journal of the American Chemical Society Jg. 137; H. 23; S. 7306 - 7309
Hauptverfasser: Hong, Allen Y., Vanderwal, Christopher D.
Format: Journal Article
Sprache:Englisch
Veröffentlicht: WASHINGTON Amer Chemical Soc 17.06.2015
Schlagworte:
Chemistry
Chemistry, Multidisciplinary
Cyclization
Indole Alkaloids - chemical synthesis
Indole Alkaloids - chemistry
Models, Molecular
Molecular Structure
Oxidation-Reduction
Physical Sciences
Science & Technology
REARRANGEMENT
(+/-)-AKUAMMICINE
CONVERSION
CYCLOADDITIONS
BIOSYNTHESIS
ASPIDOSPERMA
(+/-)-ECHITAMIDINE
(-)-VINDOLINE
NORFLUOROCURARINE
STRYCHNOS ALKALOIDS
ISSN:0002-7863, 1520-5126
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Beschreibung
Zusammenfassung:An N-oxide fragmentation/hydroxylamine oxidation/intramolecular 1,3-dipolar cycloaddition. Cascade, efficiently converted an oxidized congener of akuammicine into the complex, hexacyclic architecture of the alsmaphorazine alkaloids. This dramatic structural Change shows the chemical feasibility of our novel proposal for alsmaphorazine biogenesis, Critical to these endeavors was a marked improvement in our previously reported Zincke aldehyde cycloaddition approach to indole alkaloids, which permitted the gram--scale synthesis of akuammicine. The chemoselective oxidations of akuammicine leading tip to the key rearrangement also generated several biogenetically related alkaloids of the alstolucine and alpneumine families.
Bibliographie:NIH RePORTER
National Science Foundation
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.5b04686