- Total syntheses of marrubiin and related labdane diterpene lactones
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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.
- Kondo, Naoki,Nakamura, Seiichi,Sakagami, Yukari,Sawayama, Yuki,Yamakoshi, Hiroyuki
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- Total Syntheses of (+)-Marrubiin and (-)-Marrulibacetal
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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.
- Yamakoshi, Hiroyuki,Sawayama, Yuki,Akahori, Yoshihiro,Kato, Marie,Nakamura, Seiichi
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p. 3430 - 3433
(2016/07/26)
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