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ChemInform Abstract: Remote Control of Diels—Alder Additions. Enantioselective Synthesis of (2R)-1,2,3,4-Tetrahydro-2-hydroxy-5,8-dimethoxynaphthalen-2-yl Methyl Ketone (Wong′s Anthracycline Intermediate) from Furfural.

✍ Scribed by V. THEURILLAT-MORITZ; A. GUIDI; P. VOGEL

Publisher
John Wiley and Sons
Year
2010
Weight
35 KB
Volume
29
Category
Article
ISSN
0931-7597

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✦ Synopsis

Remote Control of Diels-Alder Additions. Enantioselective Synthesis of (2R)-1,2,3,4-Tetrahydro-2-hydroxy-5,8-dimethoxynaphthalen-2-yl Methyl Ketone (Wong's Anthracycline Intermediate) from Furfural.

-The Diels-Alder reaction of (II) with vinyl ester (III) proceeds with high regioselectivity but low enantioselectivity. The presence of Tbs-O-Tf is recommended in order to obtain smooth addition without polymerization. Compound (IV) is transformed into Wong's intermediate (VII), used for the synthesis of anthracycline anti-tumor drugs.

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