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Jatrophane Diterpenes: Preparation of the Western Fragment of Pl‐3
Author(s) -
Lentsch Christoph,
Fürst Rita,
Mulzer Johann,
Rinner Uwe
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201301616
Subject(s) - chemistry , fragment (logic) , euphorbiaceae , stereochemistry , bromide , total synthesis , combinatorial chemistry , organic chemistry , botany , computer science , biology , programming language
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 (1 R ,5 S )‐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.