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Multicomponent synthesis of 6H-dibenzo[b,d]pyran-6-ones and a total synthesis of cannabinol.

Organic letters (2011-12-17)
Penchal Reddy Nandaluru, Graham J Bodwell
ABSTRACT

A multicomponent domino reaction that affords 6H-dibenzo[b,d]pyran-6-ones is reported. The overall transformation consists of six reactions: Knoevenagel condensation, transesterification, enamine formation, an inverse electron demand Diels-Alder (IEDDA) reaction, 1,2-elimination, and transfer hydrogenation. Both the diene and dienophile for the key inverse electron demand Diels-Alder (IEDDA) step are generated in situ by secondary amine-mediated processes. In most cases, the yields (10-79%) are considerably better than those obtained using a stepwise process. This methodology is employed in a concise total synthesis of cannabinol.

MATERIALS
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Brand
Product Description

Supelco
Cannabinol solution, 1.0 mg/mL in methanol, ampule of 1 mL, certified reference material, Cerilliant®