Lasonolide A: structural revision and synthesis of the unnatural (-)-enantiomer.
Total synthesis of the unnatural (-)-enantiomer of lasonolide A was achieved starting from ethyl l-malate. The two tetrahydropyranyl fragments were prepared stereoselectively via radical cyclization reactions of beta-alkoxyacrylates. The full structure of natural lasonolide A was determined unequivocally.
Lee
Eun
E
School of Chemistry and Molecular Engineering, Seoul National University, Seoul 151-747, Korea.
Song
Ho Young
HY
Kang
Jung Won
JW
Kim
Dae-Shik
DS
Jung
Cheol-Kyu
CK
Joo
Jung Min
JM
D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis; D018942:Macrolides / Q000138:chemical synthesis*; D011161:Porifera / Q000737:chemistry / Q000378:metabolism; D013237:Stereoisomerism
D000970:Antineoplastic Agents; D018942:Macrolides; C450700:lasonolide A