Concise Synthesis of 9,11-Secosteroids Pinnigorgiols B and E
Xinghui Li, Zeliang Zhang, Huafang Fan, Yinlong Miao, Hailong Tian, Yu‐Cheng Gu, Jinghan Gui
Abstract
Pinnigorgiols B and E are 9,11-secosteroids with a unique tricyclic γ-diketone framework. Herein, we report the first synthesis of these natural products from inexpensive, commercially available ergosterol. This synthesis features a semipinacol rearrangement and an acyl radical cyclization/hemiketalization cascade; the latter efficiently assembled the tricyclic γ-diketone skeleton, with two rings and three contiguous stereogenic centers being formed in a single step.
Topics & Concepts
ChemistryStereocenterTricyclicDiketoneStereochemistryErgosterolRadical cyclizationTotal synthesisSkeleton (computer programming)Combinatorial chemistryOrganic chemistryEnantioselective synthesisCatalysisProgramming languageBiochemistryComputer scienceMarine Sponges and Natural ProductsOxidative Organic Chemistry ReactionsTraditional and Medicinal Uses of Annonaceae