Journal ArticleDOI
A New Synthetic Route to (±)-Perhydrohistrionicotoxin
TLDR
The total synthesis of the perhydrohistrionicotoxin intermediate 23 was achieved in 25% overall-yield and represents a novel method for stereospecific and position-specific introduction of a nucleophilic butyl equivalent in α-position to a ketonic carbonyl group.Abstract:
Starting from ethyl 2-cyclohexen-1-carboxylate (3) the total synthesis of the perhydrohistrionicotoxin intermediate 23 was achieved in 25% overall-yield. The two key steps involve a positionally specific addition of HOBr to the oxime-olefin 7 and the alkylation of bromooxime 17 with 1-lithio-1-butyne. The latter represents a novel method for stereospecific and position-specific introduction of a nucleophilic butyl equivalent in α-position to a ketonic carbonyl group.read more
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Der Stand der Totalsynthese zu Beginn des 21. Jahrhunderts
TL;DR: In this article, the authors stellten die Frage, welchen Stand die Totalsynthese von Naturstoffen erreicht hat, und geschildert, wie viel wir in der Wissenschaft der Totalsynthesis schon erreich haben, aber also, dass dieses Forschungsgebiet den Kinderschuhen gerade erst entschlupft.
Journal ArticleDOI
Total Synthesis and Electrophysiological Properties of Natural (−)‐Perhydrohistrionicotoxin, its Unnatural (+)‐Antipode and their 2‐Depentyl Analogs
TL;DR: In this article, the authors presented electrophysiological properties of (−)-perhydrohistrionicotoxin (6a), its unnatural (+)-antipode 6b, (−)-2-depentyl perhydro-hologrionicotin (7a), and its (+)-anti-antipodes 7b and 7b have been characterized.
Journal ArticleDOI
Manganese triacetate mediated regeneration of carbonyl compounds from oximes
TL;DR: In this article, a new method for the direct conversion of oximes into aldehydes and ketones by treatment with manganese triacetate is described, which can be used for an effective and mild oxidizing agent for the regeneration of carbonyl compounds from oximes in good yield.
Journal ArticleDOI
A total synthesis of (±)-isocomene and (±) β-isocomene by an intramolecular ene reaction
TL;DR: In this paper, the racemic sesquiterpenes isocomene 1 and β-isocomene 22 have been synthesized starting from 1,7-octadien-3-one 10 in a stereoselective manner.
Journal ArticleDOI
A carbene-yielding amino acid for incorporation into peptide photoaffinity reagents.
Lisa Beewen Shih,Hagan Bayley +1 more
TL;DR: 3-[p-[3-(Trifluoromethyl)-3H-diazirin-3-yl]phenyl]alanine has been prepared in 10 steps from p-bromobenzyl alcohol and the advantages of using this amino acid as a building block for peptide photoaffinity reagents is discussed.
References
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Journal ArticleDOI
Mixed cuprate reagents of type R1R2CuLi which allow selective group transfer
E. J. Corey,David J. Beames +1 more
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Acetylcholine Receptor and Ion Conductance Modulator Sites at the Murine Neuromuscular Junction: Evidence from Specific Toxin Reactions
Edson X. Albuquerque,Eric A. Barnard,Tieh H. Chiu,Antonio J. Lapa,J. Oliver Dolly,Sten-Erik Jansson,John W. Daly,Bernhard Witkop +7 more
TL;DR: Electrophysiological results, together with the effects of perhydrohistrionicotoxin and/or d-tubocurarine on the binding of [(3)H]monoacetyl-alpha-bungarot toxin at endplates of murine diaphragm muscle and on the bungarotoxin-elicited irreversible blockade of neuromuscular transmission, suggest that at least two types of sites participate in the synaptic excitation by acetylcholine
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The Stereochemistry of α-Haloketones. I. The Molecular Configurations of Some Monocyclic α-Halocyclanones
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