Journal ArticleDOI
Introduction of gem-dialkyl group to hexofuranose by ortho ester Claisen rearrangement.
TLDR
The ortho ester Claisen rearrangement of D-ribo- or L-lyxo- hexofuranose derivative which possesses an allyl alcohol functionality on C-3, proceeds stereoselectively to give a 3-C-dialkylated product.Abstract:
The ortho ester Claisen rearrangement of D-ribo- or L-lyxo- hexofuranose derivative which possesses an allyl alcohol functionality on C-3, proceeds stereoselectively to give a 3-C-dialkylated product. The stereochemistry of a newly introduced quaternary center of the product was unambiguously established by a chemical modification.read more
Citations
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Book ChapterDOI
Claisen Rearrangements in Carbohydrate Chemistry
Barbara Werschkun,Joachim Thiem +1 more
TL;DR: The application of the Claisen rearrangement in carbohydrate chemistry has proven a valuable method for the realization of complex synthetic schemes as mentioned in this paper, and many of the presented examples have culminated in the synthesis of novel carbohydrate mimetics or important representatives of other classes of natural products.
Journal ArticleDOI
Fluorinated allylic alcohols as building blocks
TL;DR: A theoretical study on the carbocationic reactivity of 2-fluoroallylic alcohols and derivatives explains some experimental findings as mentioned in this paper, and an outline is also given of synthetic approaches towards fluoroally-lic amines and more complex carbon skeletons starting with fluoro-allyl alcohols.
Journal ArticleDOI
Structure-activity relationships of β-hydroxyphosphonate nucleoside analogues as cytosolic 5'-nucleotidase II potential inhibitors: synthesis, in vitro evaluation and molecular modeling studies.
Maïa Meurillon,Zsuzsanna Marton,Lars Petter Jordheim,Jérôme Béjaud,Corinne Lionne,Charles Dumontet,Christian Périgaud,Laurent Chaloin,Suzanne Peyrottes +8 more
TL;DR: In this paper, β-hydroxyphosphonate nucleoside analogues incorporating modifications either on the sugar residue or the nucleobase were carried out in order to determine their potency towards the inhibition of cN-II.
Journal ArticleDOI
Synthetic studies on pactamycin, a potent antitumor antibiotic
TL;DR: In this article, two synthetic approaches to the functionalized cyclopentane core structure of pactamycin are described, one based on the Pauson-Khand reaction of an enyne prepared from diacetone-D-glucose as a chiral starting material, providing a potentially useful tricyclic intermediate for the compound and the second based on an intramolecular 1,3-dipolar cycloaddition between the nitrone and acetylene functionalities of a precursor derived from an intermediate derived from the first approach.
Journal ArticleDOI
Total, asymmetric synthesis of hexoses and azasugars branched at C(5).☆
Jürgen Wagner,Pierre Vogel +1 more
TL;DR: In this article, the Diels-Alder adduct of furan to 1-cyanovinyl (1R')-camphanate was converted into (+)-(1R,5S,6S,7S)-6-exo,7exo-(isopropylidenedioxy)-2,8-dioxabicylo[3.2.
References
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Journal ArticleDOI
Simple stereoselective version of the Claisen rearrangement leading to trans-trisubstituted olefinic bonds. Synthesis of squalene
William S. Johnson,Lucius Werthemann,William R. Bartlett,Timothy J. Brocksom,Tsung-Tee Li,D. John Faulkner,Michael R. Petersen +6 more
Journal ArticleDOI
Stereo- and regiochemistry of the Claisen rearrangement: applications to natural products synthesis
Journal ArticleDOI
Out-of-ring Claisen rearrangements are highly stereoselective in pyranoses: routes to gem-dialkylated sugars
Journal ArticleDOI
3-C-(Acylméthylène)-3-désoxy-1,2:5,6-di-O-isopropylidène-α-d-ribo- et -xylo-hexofuranoses☆
TL;DR: In this paper, a mixture of the geometrical isomers of expected α,β-unsaturated esters or of the enones was obtained in excellent yield with the keto sugar having a xylo configuration.