Total synthesis of ingenol.
A total synthesis of the biologically important diterpene ingenol has been completed. Ring-closing olefin metathesis was used to construct the strained "inside-outside" tetracyclic skeleton, and a series of diastereoselective reactions were employed to complete the synthesis. Another naturally occurring ingenane, 20-deoxyingenol, has also been prepared.
Nickel
Andrew
A
Sterling Chemistry Laboratory, Department of Chemistry, Yale University, New Haven, Connecticut 06520-8107, USA.
Maruyama
Toru
T
Tang
Haifeng
H
Murphy
Prescott D
PD
Greene
Blake
B
Yusuff
Naeem
N
Wood
John L
JL
D000498:Allyl Compounds / Q000737:chemistry; D004224:Diterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D013450:Sulfones / Q000737:chemistry
D000498:Allyl Compounds; D004224:Diterpenes; D013450:Sulfones; C008125:ingenol