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...

Full description

Saved in:
Bibliographic Details
Published in:Journal of the American Chemical Society Vol. 137; no. 23; pp. 7306 - 7309
Main Authors: Hong, Allen Y., Vanderwal, Christopher D.
Format: Journal Article
Language:English
Published: WASHINGTON Amer Chemical Soc 17.06.2015
Subjects:
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
Online Access:Get more information
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary: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.
Bibliography: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