Total synthesis of the CP-molecules (CP-263,114 and CP-225,917, phomoidrides B and A). 1. Racemic and asymmetric synthesis of bicyclo[4.3.1] key building blocks.
A brief introduction into the chemistry of the CP-molecules is followed by first-generation synthetic sequences toward key building blocks for their total synthesis. Processes for both racemic and enantiomerically enriched bicyclo[4.3.1] ketone 6 or its equivalent are described, and the absolute stereochemistries of the optically enriched intermediates are determined. The efficient route developed to racemic 6 and the ready access to both enantiomers of key building blocks provided the opportunity for the total synthesis of the CP-molecules and determination of their absolute stereochemistry.
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.
Jung
J
J
Yoon
W H
WH
Fong
K C
KC
Choi
H-S
HS
He
Y
Y
Zhong
Y-L
YL
Baran
P S
PS
D004791:Enzyme Inhibitors / Q000138:chemical synthesis*; D008299:Maleic Anhydrides / Q000138:chemical synthesis*; D013237:Stereoisomerism
C104959:CP 225917; C104957:CP 263114; D004791:Enzyme Inhibitors; D008299:Maleic Anhydrides