845724-62-1Relevant articles and documents
Synthesis and evaluation of the cytotoxicity of apoptolidinones A and D
Ghidu, Victor P.,Wang, Jingqi,Wu, Bin,Liu, Qingsong,Jacobs, Aaron,Marnett, Lawrence J.,Sulikowski, Gary A.
, p. 4949 - 4955 (2008/12/20)
(Chemical Equation Presented) Apoptolidins A-D are microbial secondary metabolites shown to be selectively cytotoxic against several cancer cell lines and noncytotoxic against normal cells. Total syntheses of apoptolidinones A and D are reported. The efficient synthetic strategy leading to the apoptolidinones features construction of the common 20-membered macrolactone by an intramolecular Suzuki reaction and stereocontrolled aldol reactions establishing the C19/C20 and C22/C23 stereocenters. In contrast to apoptolidin A, the aglycones apoptolidinone A and D were shown to be noncytotoxic when evaluated against human lung cancer cells (H292).
Total synthesis of apoptolidinone
Wu, Bin,Liu, Qingsong,Sulikowski, Gary A.
, p. 6673 - 6675 (2007/10/03)
The complex macrolide apoptolidinone (1) was synthesized in 19 steps (longest linear sequence) from (S)-malic acid. Key reactions include A) two stereoselective aldol reactions, B) a late-stage Grubbs cross-metathesis reaction to install a trisubstituted