Journal ArticleDOI
D-glycopyranosyl phenylsulfones: Their use in a stereocontrolledsynthesis of cis-2,6-disubstituted tetrahydropyrans (β-d-c-clycosides)☆
Jean-Marie Beau,Pierre Sinaÿ +1 more
TLDR
The lithiated anion derived from 3,4,6-tri-O-t-butyldimethylsilyl-2-deoxy-α, β-D-gluco-pyranosyl phenylsulfones 1 reacts with various electrophiles leading to alkylated products, precursors of β -D-C-glycosides 5−g after stereocontrolled desulfonylation and hydrolysis.About:
This article is published in Tetrahedron Letters.The article was published on 1985-01-01. It has received 61 citations till now. The article focuses on the topics: Electrophile & Benzaldehyde.read more
Citations
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Journal ArticleDOI
Total Synthesis of Aryl C-Glycoside Natural Products: Strategies and Tactics
TL;DR: The aryl C-glycoside structure is, among the plenty of biologically active natural products, one of the distinct motifs embedded, and the synthetic strategies and tactics employed in the total synthesis of this class of natural products.
Journal ArticleDOI
The chemistry and biology of the bryostatin antitumour macrolides
TL;DR: This review summarises the main developments that have occurred in bryostatin chemistry over the period 1982 to 2001 and has 117 references.
Journal ArticleDOI
Enantioselective total synthesis of altohyrtin c (spongistatin 2)
David A. Evans,B. Wesley Trotter,Paul J. Coleman,Cote Bernard,Luiz C. Dias,Hemaka A. Rajapakse,Andrew N. Tyler +6 more
TL;DR: The first total synthesis of a spongipyran macrolide, altohyrtin C, was described in this paper, which relies on a regioselective macrolactonization, a stere-lective Wittig coupling of the two major synthetic fragments, a complex anti-aldol reaction to join the C1-C15 and C16-C28 spiroketal regions, and an anomeric sulfone acylation to join C29-C37 and C38-C43 pyran regions.
References
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Journal ArticleDOI
Acyclic Stereoselective Synthesis of Carbohydrates
TL;DR: In this paper, a review examines recent syntheses of carbohydrates in which the target compounds are viewed as acyclic carbon frameworks and the synthetic approaches are divided into two categories in which critical asymmetry is placed either by stereo-selective carbon-carbon bond formation, or stereoselective carbonheteroatom bond formation.
Journal ArticleDOI
Desoxy-nitrozucker. 3. Mitteilung. Synthese von Ketosen durch Kettenverlängerung von 1-Desoxy-1-nitro-aldosen. Nucleophile Additionen und Solvolyse von Nitroaethern†
TL;DR: In this article, a nucleophilic addition of 1-deoxy-1-nitroaldoses to aldehydes and Michael acceptors and subsequent solvolytic replacement of the nitro group by a hydroxy group is described.
Journal ArticleDOI
Preparation and reactions of 2-benzenesulphonyltetrahydropyran
TL;DR: The anion derived from 2-benzenesulphonyltetrahydropyran (1) reacts with various electrophiles to give alkylated or acylated products some of which are useful precursors for spiroketal synthesis as mentioned in this paper.
Related Papers (5)
Preparation and reductive lithiation of 2-deoxy-D-glucopyranosyl phenylsulfones: A highly stereoselective route to C-glycosides☆
Jean-Marie Beau,Pierre Sinaÿ +1 more
Amelioration of the conjugate addition chemistry of .alpha.-alkoxycopper reagents: application to the stereospecific synthesis of C-Glycosides
D. K. Hutchinson,P. L. Fuchs +1 more