- Preparation of chiral 5,6-trans-disubstituted phenanthrolines from phenanthroline-5,6-epoxide
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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.
- Schoffers, Elke,Tran, Son Duc,Mace, Kristen
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p. 769 - 772
(2007/10/03)
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- The synthesis of ascididemin
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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.
- Moody, Christopher J.,Rees, Charles W.,Thomas, Robert
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p. 3589 - 3602
(2007/10/02)
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