ChemInform Abstract: Natural Products Synthesis by Retro Diels—Alder Reaction. Part 16. Total Synthesis and Structural Revision of Chromomoric Acid D-I Methyl Ester.

✍ Scribed by Z.-Y. LIU; X.-J. CHU

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 33 KB
• Volume: 30
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199904205

✦ Synopsis

Natural Products Synthesis by Retro Diels-Alder Reaction. Part 16. Total Synthesis and Structural Revision of Chromomoric Acid D-I Methyl Ester. -The first total synthesis of chromomoric acid D-1 methyl ester (XII) is presented. The synthesis includes the addition of organolithium reagent (II) to epoxyketone (I), the regio-and stereospecific reductive epoxide ring opening to the diol (IV), the retro Diels-Alder reaction of (X) to the cyclopentenone (XI), and the selective hydrogenation of the triple bond in compound (XI) to the cis-double bond in chromomoric acid D-1 methyl ester (XII) as the key steps. -(LIU, Z.-Y.;