Synthesis of an oxazoline analogue of apratoxin A.
[structure: see text] Michael addition of Me(2)Cu(CN)Li(2) to alpha,beta-unsaturated lactone 7 derived from beta-hydroxyl ketone 5 provides lactone 8, which is converted to alcohol 11 using Oppolzer's methodology as the key step. Connection of 11 with the l-proline moiety and subsequent installation of an oxazoline ring affords 16, which is coupled with tripeptide 21; subsequent macrocyclization then furnishes 4, an oxazoline analogue of apratoxin A.
Zou
Bin
B
State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, China.
Wei
Jingjun
J
Cai
Guorong
G
Ma
Dawei
D
D000970:Antineoplastic Agents / Q000138:chemical synthesis; D003500:Cyclization; D003603:Cytotoxins / Q000138:chemical synthesis*; D047630:Depsipeptides; D007659:Ketones / Q000737:chemistry; D007783:Lactones / Q000138:chemical synthesis; D008956:Models, Chemical; D015394:Molecular Structure; D010080:Oxazoles / Q000138:chemical synthesis*; D010455:Peptides / Q000737:chemistry; D010456:Peptides, Cyclic / Q000138:chemical synthesis*; D011392:Proline / Q000737:chemistry; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D013844:Thiazoles / Q000737:chemistry
D000970:Antineoplastic Agents; D003603:Cytotoxins; D047630:Depsipeptides; D007659:Ketones; D007783:Lactones; D010080:Oxazoles; D010455:Peptides; D010456:Peptides, Cyclic; D013844:Thiazoles; C442201:apratoxin A; D011392:Proline