14-Step Synthesis of (+)-Ingenol from (+)-3-Carene
2013; American Association for the Advancement of Science; Volume: 341; Issue: 6148 Linguagem: Inglês
10.1126/science.1241606
ISSN1095-9203
AutoresLars Jørgensen, Steven J. McKerrall, Christian A. Kuttruff, Felix Ungeheuer, Jakob Felding, Phil S. Baran,
Tópico(s)Phytochemical compounds biological activities
ResumoIngenol Ingenuity The diterpenoid i ngenol is the core structure of a topical drug recently commercialized to treat actinic keratosis, a precancerous skin condition. Sourcing the compound from the Euphorbia plants that produce it is relatively inefficient, so Jørgensen et al. (p. 878 , published online 1 August) devised a chemical synthesis starting from the comparatively simple and inexpensive monoterpene chiral (+)-3-carene. The synthetic sequence involves 14 steps—less than half as long as prior chemical routes to the target—and relies on a two-stage approach, inspired by the posited biosynthetic pathway, in which preliminary assembly of the fused ring framework precedes hydroxylation of the periphery.
Referência(s)