142009-82-3Relevant academic research and scientific papers
Preparation of chiral 5,6-trans-disubstituted phenanthrolines from phenanthroline-5,6-epoxide
Schoffers, Elke,Tran, Son Duc,Mace, Kristen
, p. 769 - 772 (2007/10/03)
A new preparative route to chiral aminoalcohol derivatives of 5,6-dihydro-1,10-phenanthroline is described. Ring opening of 1,10-phenanthroline-5,6-epoxide (1) with a variety of nitrogen nucleophiles was accomplished using magnesium perchlorate as an effective Lewis acid and compared to reactions catalyzed by alumina.
The synthesis of ascididemin
Moody, Christopher J.,Rees, Charles W.,Thomas, Robert
, p. 3589 - 3602 (2007/10/02)
A short synthsis of the pentacyclic marine alkaloid ascididemin 1 (four steps, 21% yield) from 1,10-phenanthroline 16 is described. The key step, photocyclisation of the quinoneimine 14 in sulphuric acid, is the first such aza stilbene photocyclisation of a quinoneimine. Intermediate 14 is prepared in a single, but low yielding, step from the quinone 4 in an aza Wadsworth-Emmons reaction, or in much better yield from the epoxide 17 by treatment with 2- iodoaniline and triethylaluminium, followed by oxidation with barium manganate.
