Cannabidiol-C-4 1 (CBD-C-4, cannabidibutol) is a natural product that is present in the extracts of Cannabis. Its isolation has not been reported to date. The aim of the proposed synthesis is to secure the availability of the pure compound, its spectroscopic characterization, and to confirm its presence in low amounts in the extracts. The enantioselective total synthesis is based on a) the use 3,5-dimetoxybenzaldehyde as starting material, b) Corey-Bakshi-Shibata reduction, c) Claisen-Ireland rearrangement, d) ring-closing metathesis, and e) completely not-trivial demethylation induced by sodium ethanethiolate.

Total Synthesis of (‐)‐Cannabidiol‐C4 / P. Marzullo, A. Maiocchi, G. Paladino, U. Ciriello, L. Lo Presti, D. Passarella. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1434-193X. - 2022:22(2022 Jun 13), pp. e202200392.1-e202200392.7. [10.1002/ejoc.202200392]

Total Synthesis of (‐)‐Cannabidiol‐C4

P. Marzullo
Primo
;
A. Maiocchi;G. Paladino;L. Lo Presti
Penultimo
;
D. Passarella
Ultimo
Conceptualization
2022-06-13

Abstract

Cannabidiol-C-4 1 (CBD-C-4, cannabidibutol) is a natural product that is present in the extracts of Cannabis. Its isolation has not been reported to date. The aim of the proposed synthesis is to secure the availability of the pure compound, its spectroscopic characterization, and to confirm its presence in low amounts in the extracts. The enantioselective total synthesis is based on a) the use 3,5-dimetoxybenzaldehyde as starting material, b) Corey-Bakshi-Shibata reduction, c) Claisen-Ireland rearrangement, d) ring-closing metathesis, and e) completely not-trivial demethylation induced by sodium ethanethiolate.
Cannabidiol; Claisen-Ireland rearrangement; Metathesis; Natural products; Total synthesis;
Settore CHIM/06 - Chimica Organica
10-mag-2022
Article (author)
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/2434/927926
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