Synthesis of the apoptosis inducing agent apoptolidin. Assembly of the C(16)-C(28) fragment.
[reaction--see text] A stereoselective synthesis of the C(16)-C(28) fragment of the apoptosis inducing agent apoptolidin is described. Key steps include two propionate aldol reactions and a stereoselective Mukaiyama aldol addition of enolsilane 19 to beta-methoxy aldehyde 4.
Sulikowski
G A
GA
Department of Chemistry, Texas A&M University, College Station, Texas 77842-3012, USA. sulikowski@mail.chem.tamu.edu
Lee
W M
WM
Jin
B
B
Wu
B
B
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology; D000903:Antibiotics, Antineoplastic / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D017209:Apoptosis / Q000187:drug effects*; D007202:Indicators and Reagents; D018942:Macrolides; D008968:Molecular Conformation; D015394:Molecular Structure; D013237:Stereoisomerism
D000900:Anti-Bacterial Agents; D000903:Antibiotics, Antineoplastic; D007202:Indicators and Reagents; D018942:Macrolides; C114125:apoptolidin