Kende, Andrew S.; Curran, Dennis P. published the artcile< Regiochemical control in dihydrophenanthrene synthesis. A photochemical total synthesis of juncusol>, Related Products of 56724-03-9, the main research area is juncusol total synthesis; phenanthrenediol dihydrodimethylvinyl Juncus total synthesis; regiochem cyclization vinylphenylbenzyl alc.
Three approaches are described toward the total synthesis of juncusol (I), a cytotoxic constituent of the needlerush Juncus roemerianus. Wittig condensation of the phosphonium salt derived from 2-methyl-3-methoxybenzyl bromide with 3-methoxy-4-methyl-5-cyanobenzaldehyde gave a mixture of cyanostilbenes, (E)- and (Z)-2,3-Me(MeO)C6H3CH:CHC6H2(CN)(OMe)Me-3,5,4. Reduction of this mixture gave the diarylethane, which failed to undergo oxidative aryl-aryl cyclization. Photocyclization of the stilbenes gave a 7:1 mixture of phenanthrenes in which the unwanted 7-cyano regioisomer predominated. The Ziegler modification of the Ullmann coupling was used to prepare the sym. dialdehyde II, which underwent successive Wittig reaction with Ph3P:CH2 and hydride reduction to give the key intermediate III. Photocyclization of III gave a dihydrophenanthrene alc. which underwent successive oxidation to an aldehyde, Wittig condensation with Ph3P:CH2, and demethylation to give I. The overall yield of I from 2-methyl-3-methoxybenzaldehyde is 18% over 10 steps; the route provides the first total synthesis of this natural product.
Journal of the American Chemical Society published new progress about Juncus roemerianus. 56724-03-9 belongs to class ethers-buliding-blocks, and the molecular formula is C9H10O2, Related Products of 56724-03-9.
Referemce:
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Ether | (C2H5)2O – PubChem