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Synthesis of (±)-Pyrenolide B

✍ Scribed by Attila Moricz; Elisabeth Gassmann; Stefan Bienz; Manfred Hesse

Book ID
102859832
Publisher
John Wiley and Sons
Year
1995
Tongue
German
Weight
528 KB
Volume
78
Category
Article
ISSN
0018-019X

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✦ Synopsis

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-oxocyclohexane-1 -carboxylate (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. ') Part of the planned Ph. D. thesis of A . A 4

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