Azorellane diterpenes from Azorella cryptantha

7-6-5 Tricarbocyclic Diterpenes

“…As can be observed in Recently, compound 56 has been isolated and characterized as the the first 9-epi-mulinane-the only mulinane with interanular junction trans-syntrans [24]. Mulinanes 36,43,46, and 54 structures have been confirmed by synthesis, as will be discussed later.…”

“…Azorellanes [14,20,[38][39][40][41][42][43][44][45][46][47][48][49][50] These compounds do not present a functionalized C-20 but in C-13 is always present an oxygenated functionality. Mulinanes show a great variety of A. compacta Antibacterial [33] 11,14-Dioxo-mulin12en-20-oic acid, 47…”

“…madreporica Antibacterial [34] Mulinone A, 50 M. crassifolium [35] Mulinone B, 51 M. crassifolium [35] biological activities, including trypanocidal, analgesic, antiinflammatory, anti-NF-kB (antinuclear factor kappa-light-chain-enhancer of activated B cells), and antituberculosis (Fig. 5.5 based in X-ray diffraction [46]. The absolute stereochemistry of azorellolide, 67, has been proposed as shown in Fig.…”

Azorella trifurcata and Mulinum echegarayii obtained from central region of<br>Argentina: antibacterial activity of their organic extracts

“…Table 1 and 2. An interesting group of bioactive metabolites, such as triterpenoids and diterpenoids with azorellane and mulinane skeletons have been obtained from Azorella, and Mulinum genera (Borquez et al,2011;Chiaramello et al, 2003a;Colloca et al,2004;Molina-Salinas et al,2010;Morales et al, 2003;Areche et al, 2009). So, some authors demonstrated that these metabolites display a wide variety of biological activities, including antimycobacterial activity (Molina-Salinas et al, 2010), trichomonicidal activity (Loyola et al, 2001), trypanocidal activity (Araya et al, 2003) and antiplasmodial activity (Loyola et al, 2004).…”

Synthesis of Mulinane Diterpenoids

“…The solvent was removed under vacuum on a rotary evaporator, and the residue was purified by column chromatography (10% EtOAc in hexanes), furnishing 705 mg (75%) of alcohol 19 and 235 mg (25%) of alcohol 20 as colorless oils. Ethyl (3R,3aS,5aS,10S,10aS,10bS)-10-Hydroxy-3-isopropyl5a,8-dimethyl-2,3,4,5,5a,6,9,10,10a,10b-decahydrocyclohepta[e]indene-3a(1H)-carboxylate (21). To a solution of alcohol 19 (807 mg, 2.14 mmol, 1.00 equiv) in 30 mL of 1,2-dichloroethane (1,2-DCE) was added Grubbs second-generation catalyst (91 mg, 0.11 mmol, 0.05 equiv), and the reaction was heated at 80°C for 6 h. After this time, a second portion of catalyst (91 mg, 0.11 mmol, 0.05 equiv) was added, and the reaction mixture was heated at 80°C for a further 18 h. 173.7, 136.4, 124.6, 70.1, 59.6, 58.4, 57.7, 53.0, 48.9, 44.1, 35.2 Ethyl (3R,3aS,5aS,10R,10aS,10bS)-10-Hydroxy-3-isopropyl5a,8-dimethyl-2,3,4,5,5a,6,9,10,10a,10b-decahydrocyclohepta[e]indene-3a(1H)-carboxylate (22).…”