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Synthesis 1995; 1995(9): 1142-1146
DOI: 10.1055/s-1995-4052
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Studies of the Furan-Terminated Cationic Cyclization: A Serendipidious Synthesis of Pallescensin A

Udo Lange, Siegfried Blechert*
  • *Institut für Organische Chemie, Sekretariat C3, Technische Universität Berlin, Straße des 17. Juni 135, D-10623 Berlin, Germany, Fax +49(30)31423619
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Publikationsdatum:
31. Dezember 2000 (online)

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The furan-terminated cationic cyclization reaction of 4-(2-furan-2-yl-2-methoxyethyl)-3,5,5-trimethylcyclohex-2-enol (3) yielded 6,6,9a-trimethyl-4,5,5a,6,7,9a-hexahydronaphtho[1,2-b]furan-4-ol (9b) in a Pictet-Spengler-like reaction thereby giving a good insight into the possible mechanism of this β-cyclization. Alcohol 9b was converted into 6,6,9a-trimethyl-7,9a-dihydro-6H-naphtho[1,2-b]furan-4-one (12), thus, completing a formal total synthesis of pallescensin A (13).

furan derivatives - cationic cyclization - pallescensin A