Journal ArticleDOI
Combination claisen-nitrile oxide annulation. a strategy for ring construction with rigid stereocontrol dictated by an allylic hydroxyl group
TLDR
In this article, a new method for annulation of rings onto existing allylic alcohol derivatives is presented, which involves Claisen rearrangement followed by nitrile oxide-olefin cycloaddition.About:
This article is published in Tetrahedron Letters.The article was published on 1985-01-01. It has received 14 citations till now. The article focuses on the topics: Claisen rearrangement & Annulation.read more
Citations
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Journal ArticleDOI
The synthesis of chiral subunits for macrolide synthesis: the Prelog-Djerassi lactone and derivatives
Robert E. Ireland,John P. Daub +1 more
TL;DR: Aus dem Dihydropyran-diol-benzaldehydacetal (Ia) erhalt man in der angegebenen Weise den als Schlusselverbindung wichtigen exocyclischen Enolether (VII) and aus ihm das Prelog-Djerassi-Lacton (VIIIb), welches Interesse bei der Synthese von Macrolid-Antibiotica besitzt as mentioned in this paper.
Book ChapterDOI
Cycloaddition Reactions of Nitrile Oxides with Alkenes
TL;DR: In this paper, a review of the cycloaddition reactions of nitrile oxides with alkenes is presented, focusing on the dramatic improvements in the degree of stereocontrol that has been attained in intermolecular reactions and to the developments in the use of intramolecular INOC reactions, where the predisposition of the reacting groups within a molecule greatly enhances the regio and stereo selectivity.
Journal ArticleDOI
Approach to tetrodotoxin via the oxidative amidation of a phenol.
TL;DR: The stereoselective introduction of a beta-hydroxynitrile functionality on one of the double bonds of the emerging dienone is achieved through an intramolecular nitrile oxide cycloaddition-fragmentation sequence.
Journal ArticleDOI
Generation of Nitrile Oxides Through O-Metalation of Hydroximoyl Chlorides. Chelation-Controlled syn-Selective Cycloaddition of Nitrile Oxides to α-Substituted Allyl Alcohols.
TL;DR: In this article, a new generation of nitrile oxides by treatment of hydroximoyl chlorides with organometallics is reported, and cycloadditions to the allyl alcohols bearing a chiral center at the 1-position proceed in a syn-selective manner.
Journal ArticleDOI
A general synthetic approach to optically active iridoid aglycones : The total syntheses of β-ethyl descarbomethoxyverbenalol, ethyl catalpol, and (-)-specionin
TL;DR: In this paper, a general approach to the synthesis of iridoid aglycones is reported, where a combination of Claisen rearrangement/nitrile oxide cycloaddition sequence has permitted the facile annulation of a highly functionalized cyclopentane ring onto a simple glycal derived from D-xylal.
References
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Journal ArticleDOI
The ester enolate Claisen rearrangement. Stereochemical control through stereoselective enolate formation
Journal ArticleDOI
The Reactions of Primary Nitroparaffins with Isocyanates1
Teruaki Mukaiyama,Toshio Hoshino +1 more
Journal ArticleDOI
Reduction of .DELTA.2-isoxazolines. 3. Raney nickel catalyzed formation of .beta.-hydroxy ketones
TL;DR: In this article, les conditions optimales de transformation d'isoxazolines-2 en β-hydroxycetones en utilisant un catalyseur Ni de Raney, l'acide borique, un melange 5/1 methanol/eau et l'hydrogene gazeux were determined.
Journal ArticleDOI
Reduction of .DELTA.2-isoxazolines: a conceptually different approach to the formation of aldol adducts
Journal ArticleDOI
Methods for the conversion of isoxazolines to β-hydroxy ketones
TL;DR: Two methods have been developed for converting isoxazolines to β-hydroxy ketones in a stereospecific manner as discussed by the authors, and one of these methods has been shown to work well in the presence of isoxal acid.
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The isoxazoline route to the hypocholesterolemic agent compactin: use of the isoxazoline as a 1,3-diene equivalent
Alan P. Kozikowski,Chun Sing Li +1 more