Jatrophane Diterpenes: Preparation of the Western Fragment of Pl-3

Jatrophane diterpenes are structurally intriguing natural products with promising biological properties. Herein, the synthesis of the western fragment of the Euphorbiaceae constituent Pl‐3 starting from (1R,5S)‐bicyclo[3.2.0]hept‐2‐en‐6‐one is described. Key steps in the sequence include a Baeyer–Vi...

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Bibliographic Details
Published in:European journal of organic chemistry 2014-02, Vol.2014 (5), p.919-923
Main Authors: Lentsch, Christoph, Fürst, Rita, Mulzer, Johann, Rinner, Uwe
Format: Article
Language:English
Subjects:
Lithium
Medicinal chemistry
Natural products
Oxidation
Terpenoids
Total synthesis
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Summary:Jatrophane diterpenes are structurally intriguing natural products with promising biological properties. Herein, the synthesis of the western fragment of the Euphorbiaceae constituent Pl‐3 starting from (1R,5S)‐bicyclo[3.2.0]hept‐2‐en‐6‐one is described. Key steps in the sequence include a Baeyer–Villiger oxidation, an iodolactonization reaction, and the installation of the northern side chain through the addition of a lithiated vinyl bromide. The overall efficiency of the route is increased by taking advantage of latent symmetry. The synthesis of the western fragment of Pl‐3 is developed by taking advantage of the latent symmetry in an intermediate; both enantiomers are thus converted into the desired substrate. Key steps of the synthesis include a Baeyer–Villiger oxidation, an iodolactonization reaction, and the addition of a vinyllithium species to the completed cyclopentane moiety of the natural product.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201301616