Asymmetric total synthesis of (-)-callystatin A employing the SAMP/RAMP hydrazone alkylation methodology.
[structure: see text] The asymmetric total synthesis of (-)-callystatin A has been achieved. The key steps generating the stereogenic centers rely on the asymmetric alpha-alkylation of aldehydes or ketones exploiting the SAMP/RAMP hydrazone alkylation methodology, as well as an enzymatic enantioselective reduction of a 3,5-dioxocarboxylate. For the construction of the alkene moieties, highly selective Wittig or Horner-Wadsworth-Emmons reactions were employed.
Vicario
Jose L
JL
Institut für Organische Chemie, Rheinisch-Westfälische Technische Hochschule, Professor Pirlet-Strasse 1, 52074 Aachen, Germany.
Job
Andreas
A
Wolberg
Michael
M
Müller
Michael
M
Enders
Dieter
D
D000478:Alkylation; D005231:Fatty Acids, Unsaturated / Q000138:chemical synthesis*; D006835:Hydrazones / Q000737:chemistry*; D013237:Stereoisomerism
D005231:Fatty Acids, Unsaturated; D006835:Hydrazones; C421091:callystatin A