title: 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.
abstract: 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.
authors.affiliation: Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA.
authors.forename: K C
authors.initials: KC
authors.lastname: Nicolaou
authors.forename: J
authors.initials: J
authors.lastname: Jung
authors.forename: W H
authors.initials: WH
authors.lastname: Yoon
authors.forename: K C
authors.initials: KC
authors.lastname: Fong
authors.forename: H-S
authors.initials: HS
authors.lastname: Choi
authors.forename: Y
authors.initials: Y
authors.lastname: He
authors.forename: Y-L
authors.initials: YL
authors.lastname: Zhong
authors.forename: P S
authors.initials: PS
authors.lastname: Baran
mesh_terms: D004791:Enzyme Inhibitors / Q000138:chemical synthesis*; D008299:Maleic Anhydrides / Q000138:chemical synthesis*; D013237:Stereoisomerism
chemical_list: C104959:CP 225917; C104957:CP 263114; D004791:Enzyme Inhibitors; D008299:Maleic Anhydrides