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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).