Total Syntheses of Clerodane Diterpenoids—A Review

Abstract

Total syntheses of clerodane diterpenoids have been reviewed from the literature since 2000.

Anti-Inflammatory and Cytotoxic Activities of Clerodane-Type Diterpenes

“…Induced apoptosis [32][33][34] Western blot Caspase activation 2,5-dihydro-5-methoxy-2-oxofuran-3-yl)ethyl]-3,4,4a,5,6,7,8,8a-octahydro-5,6,8a-trimethylnaphthalene-1-carboxylic acid); Compound 170 (methyl (4aR,5S,6R,8S,8aR)-3,4,4a,5,6,7,8,8a-octahydro-8-hydroxy-5,6,8a-trimethyl-5-[2-(2-oxo-2,5-dihydrofuran-3-yl)ethyl]naphthalene-1-carboxylate); Compound 173 (3S,4S,6S,8R,9R,12S)-3-acetoxy-18methoxycarbonyl-6,19:15,16-diepoxy-halim-5 (10),13( 16),14-triene-20,12-olide;…”

“…In this review, we have included clerodanes and neo-clerodanes and their enantiomers ent-neo-clerodanes (Figure 2). Additionally, carbons 12 to 16 are usually oxidized to diene, furan, lactone or hydrofurofuran, which give structural characteristics to clerodane [10]. Cancer is a global health problem and is currently one of the main causes contributing to premature death worldwide [11].…”

Baccharis genistelloides (Lam.) Pers. "carqueja": a review of uses in traditional medicine, phytochemical composition and pharmacological studies

“…9) fueron extraídos en extractos acuosos y orgánicos, pero para ser aislados se emplean las fracciones orgánicas de cloroformo, metanol, diclorometano, acetato de etilo y éter de petróleo (Liu et al 2020, Jünior et al 2006. Su estructura esta formada por un decahidronaftaleno y una cadena lateral de seis carbonos, de acuerdo con su estereoquímica absoluta se denominan neoclerodanos o ent-neo-clerodanos, ambos son enantíomeros y se diferencian por la posición espacial de sus sustituyentes (Hagiwara 2019, Li et al 2016, Pelot et al 2019.…”

Structural Revision of Tinotufolins from Tinospora crispa Leaves Guided by Empirical Rules and DFT Calculations

“…In our previous paper, we reported the stereochemical revision of two clerodane diterpenes isolated from the underground parts of Solidago altissima L . Clerodane diterpenes are a class of secondary metabolites with more than 1300 reported examples, which account for the majority of diterpenoids. , Some of these compounds possess biological activities such as insect antifeedant, opioid-receptor agonist, nerve growth factor-potentiating, antifungal, antibacterial, and cytotoxic. , The basic structure of clerodane diterpenes is a decalin core (C-1–C-10) with a methyl group (C-17–C-20) at C-4, C-5, C-8, and C-9 and a side-chain moiety (C-11–C-16) at C-9. These compounds are classified according to the configuration of the H 3 -19/H-10–H 3 -17/H 3 -20 fragment into four neo -clerodane types, i.e., trans – cis (TC), trans – trans (TT), cis – cis (CC), and cis – trans (CT) (Figure ).…”

“…17 activities such as insect antifeedant, opioid-receptor agonist, nerve growth factor-potentiating, antifungal, antibacterial, and cytotoxic. 17,18 The basic structure of clerodane diterpenes is a decalin core (C- 1). Their corresponding enantiomers are defined as ent-neo-clerodane.…”