alpha-Alkylidene-gamma-butyrolactone synthesis via one-pot C-H insertion/olefination: substrate scope and the total synthesis of (+/-)-cedarmycins A and B

作者：Lloyd Matthew G; D'Acunto Mariantonietta; Taylor Richard J K^*; Unsworth William P

来源：Tetrahedron, 2015, 71(39): 7107-7123.

DOI：10.1016/j.tet.2014.09.054

• C-H insertion
• Rhodium carbenoids
• alpha-Methylene-gamma-butyrolactones
• Tandem reactions
• Cedarmycins A and B

A system for the synthesis of alpha-alkylidene-gamma-butyrolactones via a one-pot C-H insertion/olefination sequence is described. The process is based on the rhodium catalysed C-H insertion reaction of alpha-diazoa-(diethoxyphosphoryl)acetates. The mild reaction conditions, operational simplicity and ready availability of starting materials are all key features. A wide range of successful reaction systems are reported (41 examples) highlighting the generality of the method. The application of this method in the total synthesis of the natural products (+/-)-cedarmycins A and B is also described.

• 出版日期2015-9-30