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

Namba Kosuke | Zendy; Kaihara Yukari | Zendy; Yamamoto Hirofumi | Zendy; Imagawa Hiroshi | Zendy; Tanino Keiji | Zendy; Williams Robert M. | Zendy; Nishizawa Mugio | Zendy

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

Author(s) -

Namba Kosuke,

Kaihara Yukari,

Yamamoto Hirofumi,

Imagawa Hiroshi,

Tanino Keiji,

Williams Robert M.,

Nishizawa Mugio

Publication year - 2009

Publication title -

chemistry – a european journal

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.687

H-Index - 242

eISSN - 1521-3765

pISSN - 0947-6539

DOI - 10.1002/chem.200900622

Subject(s) - cyclopentane , catalysis , amine gas treating , chemistry , amide , yield (engineering) , medicinal chemistry , ring (chemistry) , alcohol , stereochemistry , organic chemistry , materials science , metallurgy

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).

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