680189-50-8Relevant articles and documents
Total Synthesis of Lamellarins G, J, L, and Z Using One-Pot Halogen Dance/Negishi Coupling
Mori, Atsunori,Morii, Kazuki,Morikawa, Daiki,Okano, Kentaro,Yasuda, Yuto
, p. 13388 - 13401 (2021/10/12)
A bottom-up synthesis of lamellarins G, J, L, and Z was achieved via one-pot halogen dance/Negishi coupling of a lithiated dibromopyrrole derivative. The easily accessible dibromopyrrole bearing an ester moiety underwent halogen dance smoothly at -78 °C within 10 min. The resultant α-pyrrolyllithium was transmetalated to the corresponding organozinc species, which was then coupled with an aryl iodide in the presence of catalytic palladium to provide the fully substituted pyrrole. Subsequent halogen-lithium exchange was performed to incorporate a boronate group exclusively at the β position proximal to the ester moiety. This synthetic intermediate allowed stepwise diarylation for the total synthesis of lamellarins G, J, L, and Z.
A highly efficient synthesis of lamellarins K and L by the Michael addition/ring-closure reaction of benzyldihydroisoquinoline derivatives with ethoxycarbonyl-β-nitrostyrenes
Ploypradith, Poonsakdi,Mahidol, Chulabhorn,Sahakitpichan, Poolsak,Wongbundit, Siriporn,Ruchirawat, Somsak
, p. 866 - 868 (2007/10/03)
Alkaloid achievement: Lamellarins, a new class of potential nontoxic inhibitors of HIV-1 integrase that are also responsible for multidrug-resistance reversal in cancer cell lines, could be synthesized in three chemical steps and in 60% overall yields fro