Total synthesis of (-)-FR182877 through tandem IMDA-IMHDA reactions and stereoselective transition-metal-mediated transformations.
Intelligent design: The total synthesis of the cytotoxic (-)-FR182877 relies on 1) tandem Diels-Alder reactions to close rings A-D (see scheme), 2) a palladium-mediated 7-exo-trig reaction, and 3) an iridium-mediated isomerization followed by epimerization and stereoselective reduction.
Tanaka
Natsumi
N
Department of Chemistry and Biochemistry, Faculty of Science and Engineering, Waseda University, 3-4-1 Ohkubo, Shinjuku-ku, Tokyo 169-8555, Japan.
Suzuki
Takahiro
T
Matsumura
Takehiko
T
Hosoya
Yosuke
Y
Nakada
Masahisa
M
D006576:Heterocyclic Compounds, 4 or More Rings / Q000737:chemistry; D007495:Iridium / Q000737:chemistry; D008670:Metals / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry; D011083:Polycyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D020005:Propanols / Q000737:chemistry; D013237:Stereoisomerism
C408303:FR 182877; D006576:Heterocyclic Compounds, 4 or More Rings; D008670:Metals; D011083:Polycyclic Compounds; D020005:Propanols; C006463:allyl alcohol; D007495:Iridium; D010165:Palladium