83997-35-7Relevant academic research and scientific papers
Total Syntheses of (+)-Marrubiin and (-)-Marrulibacetal
Yamakoshi, Hiroyuki,Sawayama, Yuki,Akahori, Yoshihiro,Kato, Marie,Nakamura, Seiichi
, p. 3430 - 3433 (2016)
A stereoselective total synthesis of (+)-marrubiin has been accomplished starting from a chiral building block via the CyNH2-promoted Pauson-Khand reaction (PKR) followed by oxidative cleavage of the resultant cyclopentenone ring. Two successive oxidations and internal transacetalization culminated in the total synthesis of the antispasmodic labdane diterpenoid (-)-marrulibacetal.
Total syntheses of marrubiin and related labdane diterpene lactones
Kondo, Naoki,Nakamura, Seiichi,Sakagami, Yukari,Sawayama, Yuki,Yamakoshi, Hiroyuki
, (2020/04/10)
Total syntheses of the labdane diterpene lactones marrubiin, marrulibacetal, desertine, marrulibacetal A, marrubasch F, cyllenine C, marrulanic acid, and marrulactone are described. The trans-decalin moiety of these molecules was constructed in a stereoselective manner by a Pauson-Khand reaction, and the resultant cyclopentenone was oxidatively cleaved for formation of the lactone ring. Elongation of the side chain at C9 was achieved by an epoxide-opening reaction with a variety of nucleophiles, and the functional group manipulations completed the syntheses of these natural products. Stereochemistries of desertine could be established by the transformations.
