Total syntheses of (+/-)-montanin A and (+/-)-teuscorolide.
The first total syntheses of (+/-)-montanin A and (+/-)-teuscorolide have been achieved from an advanced precursor previously developed via a Diels-Alder strategy; in the synthetic sequence, the synthesis of montanin A was first accomplished in 8 steps, from which teuscorolide was readily achieved in 2 steps by using a novel furan oxidative cyclization-retro-cyclization process as a key operation.
Chen
I-Chia
IC
Department of Chemistry, National Tsing Hua University, Hsinchu, 30013, Taiwan.
Wu
Yen-Ku
YK
Liu
Hsing-Jang
HJ
Zhu
Jiang-Liang
JL
D003500:Cyclization; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D000439:Pentanols / Q000737:chemistry*; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D005663:Furans; D000439:Pentanols; D013141:Spiro Compounds; C533579:montanin A; C533580:teuscorolide; C015422:2,4-pentadiene-1-ol