Synthetic study of macquarimicins: highly stereoselective construction of the AB-ring system.
The highly stereoselective synthesis of the AB-ring system of macquarimicins, a novel class of microbial metabolites with inhibitory activity for neutral sphingomyelinase, has been achieved. The present synthesis features the highly stereocontrolled construction of the cis-tetrahydroindan structure via the intramolecular Diels-Alder reaction of an (E,Z,E)-1,6,8-nonatriene derived from D-glyceraldehyde acetonide. Reaction: see text.
Munakata
R
R
Department of Applied Chemistry, Keio University, Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan.
Ueki
T
T
Katakai
H
H
Takao
K I
KI
Tadano
K I
KI
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry; D000970:Antineoplastic Agents / Q000138:chemical synthesis; D004791:Enzyme Inhibitors / Q000138:chemical synthesis / Q000737:chemistry; D018942:Macrolides; D008847:Micromonospora / Q000737:chemistry; D015394:Molecular Structure; D013108:Sphingomyelin Phosphodiesterase / Q000037:antagonists & inhibitors; D013237:Stereoisomerism
D000900:Anti-Bacterial Agents; D000970:Antineoplastic Agents; D004791:Enzyme Inhibitors; D018942:Macrolides; C094822:macquarimicin A; C094823:macquarimicin B; C094824:macquarimicin C; D013108:Sphingomyelin Phosphodiesterase