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Toward Palau′amine: Hg(OTf)2-Catalyzed Synthesis of the Cyclopentane Core

✍ Scribed by Kosuke Namba; Yukari Kaihara; Hirofumi Yamamoto; Hiroshi Imagawa; Keiji Tanino; Robert M. Williams; Mugio Nishizawa

Publisher: John Wiley and Sons
Year: 2009
Tongue: English
Weight: 436 KB
Volume: 15
Category: Article
ISSN: 0947-6539
DOI: 10.1002/chem.200900622

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✦ Synopsis

Abstract

Catalytic cyclization: The Hg(OTf)~2~‐catalyzed N‐selective cyclization of amide carbonyl moieties for the construction of a quaternary carbon center was developed. The Hg(OTf)~2~‐catalyzed cyclization of cyclopentylidene alcohol with acylhydrazide afforded the desired cyclopenta[c]pyridazinone in good yield. The subsequent eight steps gave the functionalized cyclopentane with the correct stereochemistry that corresponds to the E ring of palau′amine (see scheme).magnified image

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