Total Syntheses of (+)-Marrubiin and (−)-Marrulibacetal | Zendy

Hiroyuki Yamakoshi | Zendy; Yuki Sawayama | Zendy; Yoshihiro Akahori | Zendy; Marie Kato | Zendy; Seiichi Nakamura | Zendy

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Total Syntheses of (+)-Marrubiin and (−)-Marrulibacetal

Author(s) -

Hiroyuki Yamakoshi,

Yuki Sawayama,

Yoshihiro Akahori,

Marie Kato,

Seiichi Nakamura

Publication year - 2016

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/acs.orglett.6b01602

Subject(s) - chemistry , total synthesis , cyclopentenone , stereoselectivity , stereochemistry , terpenoid , oxidative cleavage , labdane , cleavage (geology) , organic chemistry , catalysis , geotechnical engineering , fracture (geology) , engineering

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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