Total Synthesis of Theopederin D
TLDR
The total synthesis of the potent cytotoxin theopederin D has been achieved through the use of an oxidative carbon–carbon bond cleavage reaction to form an acyliminium ion in the presence of acid labile acetal groups.Abstract:
The total synthesis of the potent cytotoxin theopederin D has been achieved through the use of an oxidative carbon–carbon bond cleavage reaction to form an acyliminium ion in the presence of acid labile acetal groups Other key transformations include an acid mediated functionalization of a tetrahydrofuranyl alcohol in the presence of a tetrahydropyranyl alcohol, a syn-selective glycal epoxide opening, and a catalytic asymmetric aldehyde-acid chloride condensation.read more
Citations
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References
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Dioxiranes: synthesis and reactions of methyldioxiranes
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Catalytic Asymmetric Synthesis of tert-Butanesulfinamide. Application to the Asymmetric Synthesis of Amines
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On the direct epoxidation of glycals: application of a reiterative strategy for the synthesis of .beta.-linked oligosaccharides
TL;DR: Synthese d'oligosaccharides a partir du tri-O-acetyl-3,4,6 glucal and du dimethyl -3,3 dioxiranne as mentioned in this paper.
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1,3-Syn diastereoselective reduction of β-hydroxyketones utilizing alkoxydialkylboranes
TL;DR: Sodium borohydride reduction of β-hydroxyketones in presence of alkoxydialkylboranes 1−7 as complexing agents, produced 1,3- syn diols in at least 98:2 ratio as discussed by the authors.
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Improved Procedure for the Oxidative Cleavage of Olefins by OsO4−NaIO4
TL;DR: It is found that the addition of 2,6-lutidine can suppress the side reactions and dramatically improve the yield of this classic reaction.