Total Synthesis of (−)-Mandelalide A Exploiting Anion Relay Chemistry (ARC): Identification of a Type II ARC/CuCN Cross-Coupling Protocol

Anion relay chemistry (ARC), an effective, multicomponent union tactic, was successfully employed for the total synthesis of the highly cytotoxic marine macrolide (−)-mandelalide A (1). The northern hemisphere was constructed via a new type II ARC/CuCN cross-coupling tactic, while the southern hemis...

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Veröffentlicht in:	Journal of the American Chemical Society 2016-03, Vol.138 (11), p.3675-3678
Hauptverfasser:	Nguyen, Minh H, Imanishi, Masashi, Kurogi, Taichi, Smith, Amos B
Format:	Artikel
Sprache:	eng
Schlagworte:	Anions - chemistry chemistry Communication cytotoxicity macrolides Macrolides - chemical synthesis standard operating procedures Stereoisomerism
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container_title	Journal of the American Chemical Society
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creator	Nguyen, Minh H Imanishi, Masashi Kurogi, Taichi Smith, Amos B
description	Anion relay chemistry (ARC), an effective, multicomponent union tactic, was successfully employed for the total synthesis of the highly cytotoxic marine macrolide (−)-mandelalide A (1). The northern hemisphere was constructed via a new type II ARC/CuCN cross-coupling tactic, while the southern hemisphere was secured via a highly efficient four-component type I ARC union. Importantly, the synthesis of 1 showcases ARC as a rapid, scalable coupling strategy for the union of simple readily available building blocks to access diverse complex molecular fragments with excellent stereochemical control.
doi_str_mv	10.1021/jacs.6b01731
format	Article
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subjects	Anions - chemistry chemistry Communication cytotoxicity macrolides Macrolides - chemical synthesis standard operating procedures Stereoisomerism
title	Total Synthesis of (−)-Mandelalide A Exploiting Anion Relay Chemistry (ARC): Identification of a Type II ARC/CuCN Cross-Coupling Protocol
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