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

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

doi:10.1021/acs.orglett.6b01602

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

Hiroyuki Yamakoshi, Yuki Sawayama, Yoshihiro Akahori, Marie Kato, Seiichi Nakamura

PHA - Graduate School of Pharmaceutical Sciences (department affiliation only)

Nagoya City University

Research output: Contribution to journal › Article › peer-review

13 Citations (Scopus)

Abstract

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.

Original language	English
Pages (from-to)	3430-3433
Number of pages	4
Journal	Organic Letters
Volume	18
Issue number	14
DOIs	https://doi.org/10.1021/acs.orglett.6b01602
Publication status	Published - 2016 Jul 15

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10.1021/acs.orglett.6b01602

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abstract = "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.",

author = "Hiroyuki Yamakoshi and Yuki Sawayama and Yoshihiro Akahori and Marie Kato and Seiichi Nakamura",

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AU - Yamakoshi, Hiroyuki

AU - Sawayama, Yuki

AU - Akahori, Yoshihiro

AU - Kato, Marie

AU - Nakamura, Seiichi

PY - 2016/7/15

Y1 - 2016/7/15

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AB - 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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JO - Organic Letters

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IS - 14

ER -

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

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