Enantioselective Synthesis of (−)-Exiguolide by Iterative Stereoselective Dioxinone-Directed Prins Cyclizations
Three become one: The title compound can be prepared in 26 steps by employing a unified Prins cyclization strategy to construct both tetrahydropyran rings (see scheme). The route combines two similar dioxinone fragments and one aldehyde component to generate the core structure. (−)‐Exiguolide select...
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| Veröffentlicht in: | Angewandte Chemie International Edition 2011-09, Vol.50 (39), p.9112-9115 |
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| container_title | Angewandte Chemie International Edition |
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| creator | Crane, Erika A. Zabawa, Thomas P. Farmer, Rebecca L. Scheidt, Karl A. |
| description | Three become one: The title compound can be prepared in 26 steps by employing a unified Prins cyclization strategy to construct both tetrahydropyran rings (see scheme). The route combines two similar dioxinone fragments and one aldehyde component to generate the core structure. (−)‐Exiguolide selectively inhibits the growth of A549 cancer cells at low concentrations; the triene side chain and the Z‐enoate geometry are both necessary for this cytotoxicity. |
| doi_str_mv | 10.1002/anie.201102790 |
| format | Article |
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KGaA, Weinheim</rights><rights>Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2011 Wiley-VCH Verlag GmbH & Co. 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Chem. Int. Ed</addtitle><description>Three become one: The title compound can be prepared in 26 steps by employing a unified Prins cyclization strategy to construct both tetrahydropyran rings (see scheme). The route combines two similar dioxinone fragments and one aldehyde component to generate the core structure. 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| source | Wiley Online Library - AutoHoldings Journals; MEDLINE |
| subjects | Aldehydes - chemistry Antineoplastic Agents - chemical synthesis Antineoplastic Agents - chemistry Antineoplastic Agents - toxicity antitumor agents biological activity Cell Line, Tumor Cyclization dioxinones Humans Macrolides - chemical synthesis Macrolides - chemistry Macrolides - toxicity Prins cyclization Pyrans - chemistry Stereoisomerism total synthesis |
| title | Enantioselective Synthesis of (−)-Exiguolide by Iterative Stereoselective Dioxinone-Directed Prins Cyclizations |
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