Conversion of optically active hydrindanone to (+)-bakkenolide-A.
A total synthesis of (+)-bakkenolide-A was carried out via the key intermediate 4, which was prepared based on an asymmetric cyclization-carbonylation reaction established in our laboratory. Diastereoselective construction of the spirolactone moiety was achieved using Mitsuhashi's protocol as a key step.
Kusakabe
Taichi
T
Faculty of Pharmaceutical Sciences, Toho University, Chiba, Japan.
Kato
Keisuke
K
Motodate
Satoshi
S
Takaishi
Satoshi
S
Akita
Hiroyuki
H
D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D000972:Antineoplastic Agents, Phytogenic / Q000138:chemical synthesis*; D003500:Cyclization; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D012717:Sesquiterpenes; D013148:Spironolactone / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism
D000972:Antineoplastic Agents, Phytogenic; D007202:Indicators and Reagents; D012717:Sesquiterpenes; D013148:Spironolactone; D015107:4-Butyrolactone; C016257:bakkenolide A