4175-53-5Relevant articles and documents
A diastereoselective total synthesis of trans-trikentrin A: A ring contraction approach
Silva Jr., Luiz F.,Craveiro, Marcus V.
body text, p. 5417 - 5420 (2009/06/06)
(Chemical Equation Presented) A new route to obtain the polyalkylated indole (±)-trans-trikentrin A was developed. The synthesis of this natural alkaloid features a thallium(III)-mediated ring contraction reaction to obtain the trans-1,3-disubstituted five-membered ring in a diastereoselective manner. Thallium(III) is chemoselective in this rearrangement, reacting with the olefin without oxidation of the indole moiety. Other key transformations are the Bartoli's reaction to construct the heterocyclic ring and a Heck coupling to add the carbons atom that will originate the nonaromatic cycle.
Total synthesis of (±)-iso-trans-trikentrin B
MacLeod, John K.,Ward, Annemarie,Willis, Anthony C.
, p. 177 - 187 (2007/10/03)
The synthesis of the title compound, a member of a family of cyclopent[g]indoles isolated from a marine sponge, is described. Most of the synthetic sequence was developed starting from the more readily available cis-l,3-dimethylindan. An X-ray crystal structure of the indanol (24), the precursor of trns-1,3-dimethylindan, confirmed its relative stereochemistry.
The Total Synthesis of (+/-)-cis- and trans-Trikentrin A
MacLeod, John K.,Monahan, Lilian C.
, p. 329 - 337 (2007/10/02)
The synthesis of the title compounds, which are novel cyclopentindoles isolated from a marine sponge Trikentrion flabelliforme, is described.An aryl radical cyclization and a 1,5-electrocyclic reaction of a nitrene are key steps in formation of the two
