Total Synthesis of the Cytostatic Marine Natural Product
Dibromophakellstatin via Three-Component Imidazolidinone
Anellation
Michael Zöllinger
Peter Mayer
Thomas Lindel
10.1021/jo061813u.s008
https://acs.figshare.com/articles/dataset/Total_Synthesis_of_the_Cytostatic_Marine_Natural_Product_Dibromophakellstatin_via_Three_Component_Imidazolidinone_Anellation/3042796
The tetracyclic pyrrole−imidazole alkaloid dibromophakellstatin from the marine sponge <i>Phakellia
</i><i>mauritiana</i> has been synthesized within seven steps from pyrrole in an 18% overall yield. The key step
is a three-component assembly of a tricyclic enamide, a nitrene, and a carbamoyl building block, affording
the imidazolidinone ring of dibromophakellstatin in one step. Notably, it is possible to employ the reagent
EtO<sub>2</sub>CNHOTs in a double function as a source of the electrophilic nitrene and of a dipolar carbamoyl
component. Use of debrominated precursor dipyrrolopyrazinones leads to much higher anellation yields
and allowed us to develop a second generation synthesis. The cytostatic activity of dibromophakellstatin
is confirmed.
2006-12-08 00:00:00
dipolar carbamoyl component
Cytostatic Marine Natural Product Dibromophakellstatin
pyrrole
marine sponge Phakellia mauritiana
electrophilic nitrene
generation synthesis
anellation yields
reagent EtO 2CNHOTs
imidazolidinone ring
carbamoyl building block
dibromophakellstatin
cytostatic activity
debrominated precursor dipyrrolopyrazinones
Total Synthesis
tricyclic enamide