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Sulikowski Lab

Progress toward the total synthesis of lucentamycin A: total synthesis and biological evaluation of 8-epi-lucentamycin A.

AUTHORS

Daniels RNR Nathan , Melancon BJ Bruce J , Wang EA Emily A , Crews BC Brenda C , Marnett LJ Lawrence J , Sulikowski GA Gary A , Lindsley CW Craig W . The Journal of organic chemistry. 2009 11 20; 74(22). 8852-5

ABSTRACT

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.

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.