Total Synthesis of Thiostrepton, Part 1: Construction of the Dehydropiperidine/Thiazoline-Containing Macrocycle

A cornerstone of the RNA‐binding antibiotic thiostrepton, namely the dehydropiperidine–thiazoline macrocyclic domain (see formula), was constructed through a hetero‐Diels–Alder‐type dimerization of an azadiene and selective elaboration of the resulting dehydropiperidine system.

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Veröffentlicht in:Angewandte Chemie International Edition 2004-09, Vol.43 (38), p.5087-5092
Hauptverfasser: Nicolaou, K. C., Safina, Brian S., Zak, Mark, Estrada, Anthony A., Lee, Sang Hyup
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container_issue 38
container_start_page 5087
container_title Angewandte Chemie International Edition
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creator Nicolaou, K. C.
Safina, Brian S.
Zak, Mark
Estrada, Anthony A.
Lee, Sang Hyup
description A cornerstone of the RNA‐binding antibiotic thiostrepton, namely the dehydropiperidine–thiazoline macrocyclic domain (see formula), was constructed through a hetero‐Diels–Alder‐type dimerization of an azadiene and selective elaboration of the resulting dehydropiperidine system.
doi_str_mv 10.1002/anie.200461340
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subjects antibiotics
azadienes
cycloaddition
Macrocyclic Compounds - chemical synthesis
Molecular Conformation
natural products
Piperidines - chemical synthesis
Piperidines - chemistry
Thiazoles - chemical synthesis
Thiazoles - chemistry
Thiostrepton - chemical synthesis
total synthesis
title Total Synthesis of Thiostrepton, Part 1: Construction of the Dehydropiperidine/Thiazoline-Containing Macrocycle
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