Total Synthesis of Shensongine A
Sean Kerwin describes the total synthesis of the pyrrole spiroketal alkaloid shensongine A.
N-Alkynyl Pyrrole Based Total Synthesis of Shensongine A: B. J. Reinus, S. M. Kerwin
Synthesis 2019, DOI: 10.1055/s-0037-1611904
Shensongine A belongs to a family of natural products known as pyrrole spiroketal alkaloids, which have been isolated from different sources and present a range of interesting biological activities. These compounds have also a place in traditional Chinese medicine, but the systematic study of shensongine A and its congeners has been hindered by the small amounts available from natural sources. The group of Professor Sean Kerwin from Texas State University (USA) has recently reported a new total synthesis of the title compound.
Professor Kerwin said: “In our ongoing efforts exploiting the versatile chemistry of N-alkynyl azoles, we have completed the total synthesis of the spirocyclic pyrrole natural product shensongine A in 11 steps by employing a gold-catalyzed cyclization of an advanced N-alkynyl pyrrole intermediate.”