77844-26-9Relevant articles and documents
Total syntheses of (-)-haemanthidine, (+)-pretazettine, and (+)-tazettine
Baldwin, Steven W.,Debenham, John S.
, p. 99 - 102 (2000)
(matrix presented) Haemanthidine Pretazettine Tazettine The total syntheses of the amaryllidaceae alkaloids haemanthidine, pretazettine, and tazettine as optically pure enantiomers are reported. Using D-mannose as the starting material, the critical relat
First Asymmetric Total Syntheses of (+)-Crinamine, (-)-Haemanthidine, and (+)-Pretazettine
Nishimata, Toyoki,Mori, Miwako
, p. 7586 - 7587 (2007/10/03)
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Phenolic Oxidative Coupling with Hypervalent Iodine. A Synthesis of 6a-Epipretazettine
White, James D.,Chong, Wesley K. M.,Thirring, Klaus
, p. 2300 - 2302 (2007/10/02)
6a-Epipretazettine was synthesized in seven steps from piperonal and synephrine.Intramolecular, monophenolic, oxidative coupling of a functionalized benzylic acetal, employing benzene as oxidant, gave a spirodienone in 13 percent yield.Subsequent deprotection of the secondary amine was followed by spontaneous closure to a tetracyclic pyrrolidine possessing an all-cis ring fusion.This substance was reduced with diisobutylaluminum hydride, and the resulting alcohol was transformed, via methanolysis of the corresponding mesylate, to O-methyl-6a-epipretazettine.Acidic hydrolysis of the latter yielded 6a-epipretazettine, identical with material previously obtained by Danishefsky.