Synthesis of Bodinieric Acids A and B, Both C-18 and C-19-functionalized Abietane Diterpenoids: DFT Study of the Key Aldol Reaction

Overview

Journal RSC Adv

Publisher Royal Society of Chemistry

Specialty Chemistry

Date 2022 May 2

PMID 35497114

Authors

Ramon J Zaragoza

Miguel A Gonzalez-Cardenete

Affiliations

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Abstract

The first synthesis of C-18- and C-19-bifunctionalized abietane diterpenoids, bodinieric (or callicapoic) acids, an aldol reaction has been developed. This key aldol reaction was very sensitive to steric hindrance. This fact has been studied by deuterium exchange experiments and DFT methods. Optimization of this reaction led to the synthesis of anti-inflammatory bodinieric acids A and B, starting from abietic acid.

Citing Articles

Total synthesis of naturally occurring abietane diterpenoids a late-stage Fe(iii)-TAML catalysed Csp-H functionalization.

Munda M, Chatterjee D, Majhi M, Biswas S, Pal D, Bisai A RSC Adv. 2024; 14(28):20420-20424.

PMID: 38932981 PMC: 11200212. DOI: 10.1039/d4ra03791j.

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