Total Syntheses of (+)-Marrubiin and (−)-Marrulibacetal
2016
Yamakoshi, Hiroyuki | Sawayama, Yuki | Akahori, Yoshihiro | Kato, Marie | Nakamura, Seiichi
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.
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