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Synthesis of $\pm$-pyrenolide B


Moricz, Attila; Gassmann, Elisabeth; Bienz, Stefan; Hesse, Manfred (2004). Synthesis of $\pm$-pyrenolide B. Helvetica Chimica Acta, 78(3):663-669.

Abstract

In the synthesis of the title compound 12, the important intermediate 7 was obtained in good yield from the easily available ethyl 5,5-ethylenedioxy-2-oxocyclohexane1 --c arboxylate (1) via ring enlargement of the bicyclic enol ether 5 (Scheme). Its reduction (NaBH,, CeCI, in EtOH) and subsequent protection with (t-Bu)Me2Si resulted in the highly functionalized ten-membered lactone 9. Introduction of the (2)-configurated double bond, followed by deprotection and elimination of H20, gave (A)-pyrenolide B (12) in 16% overall yield.

Abstract

In the synthesis of the title compound 12, the important intermediate 7 was obtained in good yield from the easily available ethyl 5,5-ethylenedioxy-2-oxocyclohexane1 --c arboxylate (1) via ring enlargement of the bicyclic enol ether 5 (Scheme). Its reduction (NaBH,, CeCI, in EtOH) and subsequent protection with (t-Bu)Me2Si resulted in the highly functionalized ten-membered lactone 9. Introduction of the (2)-configurated double bond, followed by deprotection and elimination of H20, gave (A)-pyrenolide B (12) in 16% overall yield.

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:English
Date:2004
Deposited On:25 Aug 2017 13:19
Last Modified:25 Aug 2017 13:19
Publisher:Wiley-Blackwell Publishing, Inc.
ISSN:0018-019X
Publisher DOI:https://doi.org/10.1002/hlca.19950780313

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