Synthesis of  rac ‐Midpacamide and the  spiro ‐Cyclization of Its Precursor | Zendy

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Synthesis of rac ‐Midpacamide and the spiro ‐Cyclization of Its Precursor

Author(s) -

Lindel Thomas,

Hoffmann Holger

Publication year - 1997

Publication title -

liebigs annalen

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 0947-3440

DOI - 10.1002/jlac.199719970731

Subject(s) - chemistry , moiety , pyrrole , hydantoin , acetic acid , natural product , bromine , ring (chemistry) , ruthenium , catalysis , organic chemistry , combinatorial chemistry , medicinal chemistry

The alkylidene hydantoin 8 was synthesized as an analogue of the marine natural product oroidin ( 1 ) by employing a Horner‐Wadsworth‐Emmons reaction. Treatment of 8 with bromine in acetic acid induced a biomimetic spiro ‐cyclization forming the ACD ring system of dibromophakellin ( 2 ) in one step. rac ‐Midpacamide ( 10 ) was obtained from the same precursor through a chemoselective, ruthenium‐catalyzed hydrogenation leaving the brominated pyrrole moiety intact.

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