View source for Birman's synthesis of sceptrin

Sceptrin is a useful naturally occurring product found in ''Agelas sceptrum'', 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]], an alkaloid poison found in certain fungi.

== Retrosynthesis ==
[[Image:Synthesis_of_Sceptrin_IV.png|800px|Retrosynthetic analysis of Sceptrin‎]]

== Synthesis of Starting compound ==
[[Image:Synthesis_of_Sceptrin_III.png|800px|Synthesis of Sceptrin‎ starting material]]

== Synthesis of Sceptrin (2nd Generation) ==
[[Image:‎Synthesis_of_Sceptrin.png|800px|Total synthesis of Sceptrin‎, part 1]]

[[Image:Synthesis_of_Sceptrin_II.png|800px|Total synthesis of Sceptrin‎‎, part 2]]

== Inside the synthesis ==
The starting four member ring is made via a [2+2] addition in the presence of UV light. In step 3 of the synthesis, the KOH/MeOH changed the orientation of carbon atom in the first position from cis to trans. Guanidine was added in DMF to convert the bromoacetyl groups into [[imidazole]] rings. The addition of PPh<sub>3</sub> in NH<sub>3</sub> fosters the change of the azides into amines.

== Conclusions ==
It should also be noted that the compound is stereoselective. An interesting feature of this compound lies in the fact that the central ring is a [[cyclobutane]] ring, which in usual circumstances is not very stable due to ring strain.  The overall synthesis of sceptrin is convergent.

==References==
# {{citation | last1 = Birman | first1 = Vladimir B. | last2 = Jiang | first2 = Xun-Tian | title = Synthesis of Sceptrin Alkaloids | journal = Org. Lett. | year = 2004 | volume = 6 | issue = 14 | pages = 2369–71 | doi=10.1021/ol049283g}}.
# {{citation | last1 = Baran | first1 = Phil S. | last2 = Zografos | first2 = Alexandros L. | last3 = O'Malley | first3 = Daniel P. | title = Short Total Synthesis of (±)-Sceptrin | journal = J. Am. Chem. Soc. | year = 2004 | volume = 126 | issue = 12 | pages = 3726–27 | doi=10.1021/ja049648s}}.
# {{citation | last1 = Walker | first1 = Roger P. | last2 = Faulkner | first2 = D. John | first3 = Donna | last3 = Van Engen | first4 = Jon | last4 = Clardy | title = Sceptrin, an antimicrobial agent from the sponge ''Agelas sceptrum'' | journal = J. Am. Chem. Soc. | year = 1981 | volume = 103 | page = 6772–73 | doi = 10.1021/ja00412a052}}.

[[Category:Chemistry 444 pages]]
[[Category:Total syntheses]]