Regiochemical control in the diels alder reactions of substituted naphthoquinones: Orientational manipulation in the synthesis of anthraquinones.

✍ Scribed by T.Boss Kelly

• Publisher: Elsevier Science
• Year: 1978
• Tongue: French
• Weight: 261 KB
• Volume: 19
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)94552-6

✦ Synopsis

In conjunction with ongoing studies directed toward the development of a regiospecific synthesis of adriamycin, we recently advanced' a rationale for the regiochemical outcome of Diels Alder reactions between unsymmetric dienes and some oxygenated naphthoquinones. We now report the result of additional experiments which a) corroborate this hypothesis, b) illustrate its ability to predict regiochemical consequences and c) demonstrate how in a specific instance the Constitution of an oxygenated naphthoquinone can be manipulated to obtain a desired regioisomer.

In the course of other work, it was desirable to devise a regiochemically controlled route to molecules possessing structures and substitution patterns such as those found in 1 -