Total synthesis of lucilactaene, a cell cycle inhibitor active in p53-inactive cells.
Hetero-bis-metalated 1,3-butadiene is employed in the lynchpin coupling of synthetic fragments of the side chain of the antitumor agent, lucilactaene. Sequential Stille and Suzuki-Miyaura couplings interpolate this unique boron/tin diene into the pentaene chain. The total synthesis of lucilactaene was accomplished efficiently, in just eight linear steps.
Coleman
Robert S
RS
Department of Chemistry, The Ohio State University, 100 West 18th Avenue, Columbus, Ohio 43210-1185, USA. coleman@chemistry.ohio-state.edu
Walczak
Matthew C
MC
Campbell
Erica L
EL
D002453:Cell Cycle / Q000187:drug effects*; D002477:Cells / Q000737:chemistry / Q000378:metabolism*; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D015394:Molecular Structure; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D016159:Tumor Suppressor Protein p53 / Q000172:deficiency*
D005663:Furans; D011758:Pyrroles; D016159:Tumor Suppressor Protein p53; C444204:lucilactaene