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Synthetic studies on lemonomycin: construction of the tetracyclic core.

ABSTRACT: A substrate-induced stereocontrol strategy was used to gain access to the tetracyclic core of (-)-lemonomycin. An advanced intermediate was prepared from a known substituted tyrosinol through a 16-step sequence, which involved a Pictet-Spengler reaction, a [3+2] dipolar cycloaddition and an enamide hydrogenation.

SUBMITTER: Jimenez-Somarribas A

PROVIDER: S-EPMC4114395 | biostudies-literature | 2013 Sep

REPOSITORIES: biostudies-literature

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Synthetic studies on lemonomycin: construction of the tetracyclic core.

Jiménez-Somarribas Alberto A Williams Robert M RM

Tetrahedron 20130901 35

A substrate-induced stereocontrol strategy was used to gain access to the tetracyclic core of (-)-lemonomycin. An advanced intermediate was prepared from a known substituted tyrosinol through a 16-step sequence, which involved a Pictet-Spengler reaction, a [3+2] dipolar cycloaddition and an enamide hydrogenation. ...[more]

PMID: 25083002

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