1623755-25-8Relevant articles and documents
Light-mediated total synthesis of 17-deoxyprovidencin
Toelle, Nina,Weinstabl, Harald,Gaich, Tanja,Mulzer, Johann
, p. 3859 - 3862 (2014/05/06)
An asymmetric synthesis of the diterpenoid 17-deoxyprovidencin is described. Key steps include an aldol addition, a base-catalyzed Wipf-type furan formation, a Z-selective ring-closing metathesis for macrocyclization, a photochemical E/Z isomerization to a highly strained and conformationally restricted ring system, and the stereoselective formation of two epoxides on the ring. Photochemistry is the key: An asymmetric synthesis of the diterpenoid 17-deoxyprovidencin is described. Key steps include an aldol addition, a base-catalyzed Wipf-type furan formation, a Z-selective ring-closing metathesis for macrocyclization, a photoinduced Z/E isomerization to a highly strained conformationally restricted ring system, and the stereoselective formation of two epoxides on the macrocycle.
