Novel strategies to construct the gamma-hydroxy lactone moiety of the CP molecules. Synthesis of the CP-225,917 core skeleton.
[formula: see text] The array of challenging structural lineaments embodied in the CP molecules (1 and 2, Figure 1) offers synthetic chemists uncharted realms of exploration and discovery. In this communication, we focus on the chemical hurdies posed by the gamma-hydroxy lactone moiety of these exciting targets. Thus, the examination of the general reactivity of these systems, the development of a novel tandem oxidation sequence to construct the gamma-hydroxy lactone moiety, and the successful construction of the complete polycyclic core of 2 (compound 28, Scheme 5) is enumerated within.
Nicolaou
K C
KC
Department of Chemistry, Scripps Research Institute, La Jolla, California, USA. kcn@scripps.edu
He
Y
Y
Fong
K C
KC
Yoon
W H
WH
Choi
H S
HS
Zhong
Y L
YL
Baran
P S
PS
D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry; D007202:Indicators and Reagents; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D008299:Maleic Anhydrides / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D010084:Oxidation-Reduction
C104959:CP 225917; D004791:Enzyme Inhibitors; D007202:Indicators and Reagents; D007783:Lactones; D008299:Maleic Anhydrides