Total synthesis of zyzzyanones A-D.

Autor: Nadkarni DH; Department of Chemistry, University of Alabama at Birmingham, 901 14 Street South, Birmingham, Alabama 35294, USA., Murugesan S, Velu SE
Jazyk: angličtina
Zdroj: Tetrahedron [Tetrahedron] 2013 May 20; Vol. 69 (20), pp. 4105-4113.
DOI: 10.1016/j.tet.2013.03.052
Abstrakt: Zyzzyanones A-D is a group of biologically active marine alkaloids isolated from Australian marine sponge Zyzzya fuliginosa . They contain a unique bispyrroloquinone ring system as the core structure. The first total synthesis of all four zyzzyanones is described here. The synthesis of these alkaloids started from a previously known 6-benzylamino indole-4,7-quinone derivative and involves 6-7 steps. The key step in the synthesis involves the construction of a pyrrole ring in one step using a Mn(OAc) 3 mediated oxidative free radical cyclization reaction of a 6-benzylamino indole-4,7-quinone derivative with 4-benzyloxyphenyl acetaldehyde diethyl acetal in CH 3 CN.
Databáze: MEDLINE