Birman's synthesis of sceptrin

Background

        Sceptrin is a useful naturally occurring product. found Agelas sceptrum, which is a sponge that inhabits the Glover Reef in Belize. The chemical has anti-bacterial, antiviral, and anti-histaminic properties. Sceptrin also has anti-muscarinic properties. The term muscarinic is derived from Muscarine, which is an alkaloid poison found in certain fungi.

Synthesis of Sceptrin (2nd Generation)

File:Synthesis of Sceptrin II.jpg

References

1. Birman, V. B.; Jiang, X.-T., "Synthesis of Sceptrin Alkaloids," Org. Lett. 2004 6(14); 2369-2371. DOI: 10.1021/ol049283g
2. Baran, P. S.; Zografos, A. L.; O'Malley, D. P. "Short Total Synthesis of (±)-Sceptrin" J. Am. Chem. Soc. 2004 126(12); 3726-3727. DOI: 10.1021/ja049648s