Concepedia

Short, Enantioselective Total Synthesis of Sceptrin and Ageliferin by Programmed Oxaquadricyclane Fragmentation

Phil S. Baran, Ke Li, Daniel P. O’Malley, Christos Mitsos

Angewandte Chemie International Edition · 2005 · 78 citations · 19 references

Abstract

Absolutely without auxiliaries: The enantioselective syntheses of both enantiomers of the dimeric pyrrole–imidazole alkaloids sceptrin and ageliferin have been achieved by a non-auxiliary-based route, which allows assignment of the absolute configuration of natural ageliferin. The “programming” of the oxaquadricyclane fragmentation leading to enantiopure tetrasubstituted cyclobutanes is the crucial step in the synthesis.

References

19

4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methyl-morpholinium chloride: an efficient condensing agent leading to the formation of amides and esters

Munetaka Kunishima, Chiho Kawachi, Jun Monta et al. · Tetrahedron · 1999 · 469 citations

Engineering, Organic Chemistry, Synthetic Chemistry +5

Sceptrin, an antimicrobial agent from the sponge Agelas sceptrum

Roger P. Walker, D. John Faulkner, Donna Van Engen et al. · Journal of the American Chemical Society · 1981 · 227 citations

Bioorganic Chemistry, Altmetric Attention Score, Sponge Agelas Sceptrum +17

Bioactive bromopyrrole metabolites from the Caribbean sponge Agelas conifera

Paul A. Keifer, Robert E. Schwartz, Moustapha E. S. Koker et al. · The Journal of Organic Chemistry · 1991 · 175 citations

Biosynthesis, Biochemistry, Bioactive Bromopyrrole Metabolites +12

Sceptrin as a Potential Biosynthetic Precursor to Complex Pyrrole–Imidazole Alkaloids: The Total Synthesis of Ageliferin

Phil S. Baran, Daniel P. O’Malley, Alexandros L. Zografos · Angewandte Chemie International Edition · 2004 · 128 citations

Medicinal Chemistry, Bioorganic Chemistry, Microwave-induced Magic +13

Short Total Synthesis of (±)-Sceptrin

Phil S. Baran, Alexandros L. Zografos, Daniel P. O’Malley · Journal of the American Chemical Society · 2004 · 119 citations