Progress toward the total synthesis of lucentamycin A: total synthesis and biological evaluation of 8-epi-lucentamycin A.
Synthetic efforts toward the cytotoxic peptides lucentamycins A-D are described that resulted in the total synthesis and biological evaluation of 8-epi-lucentamycin A in 15 steps with 2.2% overall yield. The key epi-nonproteogenic 3-methyl-4-ethylideneproline was synthesized via a titanium-mediated cycloisomerization reaction.
Daniels
R Nathan
RN
Department of Chemistry, Vanderbilt University, Nashville, Tennessee 37232, USA.
Melancon
Bruce J
BJ
Wang
Emily A
EA
Crews
Brenda C
BC
Marnett
Lawrence J
LJ
Sulikowski
Gary A
GA
Lindsley
Craig W
CW
D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D020128:Inhibitory Concentration 50; D008968:Molecular Conformation; D009842:Oligopeptides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology* / Q000633:toxicity; D013237:Stereoisomerism
D000970:Antineoplastic Agents; D009842:Oligopeptides; C523222:lucentamycin A