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

Penchal Reddy Nandaluru; Graham J Bodwell

doi:10.1021/ol2030636

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

Org Lett. 2012 Jan 6;14(1):310-3. doi: 10.1021/ol2030636. Epub 2011 Dec 15.

Authors

Penchal Reddy Nandaluru¹, Graham J Bodwell

Affiliation

¹ Department of Chemistry, Memorial University, St. John's, NL, Canada, A1B 3X7.

PMID: 22172052
DOI: 10.1021/ol2030636

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Cannabinol / chemical synthesis*
Hydrogenation
Lactones / chemical synthesis*
Molecular Structure
Phenanthrenes / chemical synthesis*
Pyrans

Substances

Lactones
Phenanthrenes
Pyrans
6H-dibenzo-(b,d)-pyran-6-one
Cannabinol