Total synthesis of the CP-molecules (CP-263,114 and CP-225,917, phomoidrides B and A). 2. Model studies for the construction of key structural elements and first-generation strategy.
Crucial model synthetic and mechanistic studies directed toward the development of methodology for the construction of the maleic anhydride moiety of the CP-molecules are described. Studies directed toward the stereoselective attachment of the upper side chain, culminating in the discovery of long-range stereochemical control, are also discussed. In addition, a first-generation strategy toward the CP-molecules, establishing key intermediate 5 as a "beachhead" from which all future operations would diverge, is also presented. Although this first-generation strategy failed to yield the target molecules, the endeavor laid the important groundwork for the next-generation drives toward the CP-molecules.
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.
Baran
P S
PS
Zhong
Y-L
YL
Fong
K C
KC
Choi
H-S
HS
D004791:Enzyme Inhibitors / Q000138:chemical synthesis*; D008299:Maleic Anhydrides / Q000138:chemical synthesis*; D008958:Models, Molecular; D013237:Stereoisomerism
C104959:CP 225917; C104957:CP 263114; D004791:Enzyme Inhibitors; D008299:Maleic Anhydrides