Jatrophane diterpenes: Preparation of the western fragment of pl-3

Christoph Lentsch, Rita Fürst, Johann Mulzer, Uwe Rinner*

*المؤلف المقابل لهذا العمل

نتاج البحث: المساهمة في مجلةArticleمراجعة النظراء

10 اقتباسات (Scopus)

ملخص

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.

اللغة الأصليةEnglish
الصفحات (من إلى)919-923
عدد الصفحات5
دوريةEuropean Journal of Organic Chemistry
مستوى الصوت2014
رقم الإصدار5
المعرِّفات الرقمية للأشياء
حالة النشرPublished - فبراير 2014
منشور خارجيًانعم

ASJC Scopus subject areas

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