Lasonolide A: structural revision and total synthesis.
The proposed structure of lasonolide A was synthesized employing radical cyclization reactions of beta-alkoxyacrylates for preparation of the tetrahydropyranyl units A and B, but the spectroscopic data did not match those of the natural product. Both enantiomers of a revised structure featuring 17E,25Z double bonds were synthesized, and the (-)-isomer was found to be the biologically active enantiomer.
Song
Ho Young
HY
School of Chemistry and Molecular Engineering, Seoul National University, Seoul 151-747, Korea.
Joo
Jung Min
JM
Kang
Jung Won
JW
Kim
Dae-Shik
DS
Jung
Cheol-Kyu
CK
Kwak
Hyo Shin
HS
Park
Jin Hyun
JH
Lee
Eun
E
Hong
Chang Yong
CY
Jeong
ShinWu
S
Jeon
Kiwan
K
Park
Ji Hyun
JH
D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D002455:Cell Division / Q000187:drug effects; D003500:Cyclization; D006801:Humans; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D015394:Molecular Structure; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D014407:Tumor Cells, Cultured
D000970:Antineoplastic Agents; D018942:Macrolides; C450700:lasonolide A