Iodine(V) reagents in organic synthesis. Part 2. Access to complex molecular architectures via Dess-Martin periodinane-generated o-imidoquinones.
o-Imidoquinones, a rather rare class of compounds, are prepared from anilides by the action of Dess-Martin periodinane (DMP) and water. Their chemistry has been extensively investigated and found to lead to p-quinones and polycyclic systems of diverse molecular architectures. Applications of this methodology to the total synthesis of the naturally occurring compounds, epoxyquinomycin B and BE-10988, are described. Finally, another rare chemical entity, the ketohydroxyamide moiety, has been accessed through this DMP-based synthetic technology, and its reactivity has been studied. Among its most useful reactions is a set of cascade heterocyclic annulations leading to a variety of polycyclic systems of possible biological relevance.
Nicolaou
K C
KC
Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA.
Sugita
K
K
Baran
P S
PS
Zhong
Y-L
YL
D000475:Alkenes / Q000737:chemistry; D000813:Anilides / Q000737:chemistry; D018360:Crystallography, X-Ray; D004852:Epoxy Compounds / Q000737:chemistry; D007455:Iodine / Q000737:chemistry*; D015394:Molecular Structure; D010084:Oxidation-Reduction; D011809:Quinones / Q000138:chemical synthesis* / Q000737:chemistry
D000475:Alkenes; D000813:Anilides; D004852:Epoxy Compounds; D011809:Quinones; D007455:Iodine