Oxidation of several triterpenic diene and triene systems. Oxidative cleavage to obtain chiral intermediates for drimane and phenanthrene semi-synthesis

Garcı́a-Granados, Andrés; López, Pilar; Melguizo, Enrique; Parra, Andrés; Simeó, Yolanda

doi:10.1016/j.tet.2004.03.008

Cited by 20 publications

(15 citation statements)

References 27 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Compound 23, a ketoepoxy synthon from the A-and B-rings, had a C 14 skeleton and is an adequate precursor for the synthesis of drimane and related compounds. The other compounds obtained, 24 [18] and 25, presented a C 16 skeleton from the D-and E-rings of the triterpene skeleton.…”

mentioning

confidence: 95%

“…Treatment of compound 21 with RuCl 3 /NaIO 4 in acetone/H 2 O at room temperature for 30 min gave a mixture of two aldehyde sesquiterpenes (32 and 33, [18]), one of which, drim-8-en-11-al (32), has been used as an appropriate synthon to produce other remarkable drimane-related compounds [23] 4. Reactivity of Fragments 12, 32, and 33: Partial Syntheses of Ambrox and cisDecalin Synthons.…”

mentioning

confidence: 99%

“…Maslinic acid (2) was isolated from the solid waste of olive-oil pressing which was extracted in a Soxhlet apparatus with AcOEt. It was purified from these mixtures by CC over SiO 2 and transformed with ethereal CH 2 N 2 or NaOH/MeI into the corresponding methyl ester which was deoxygenated in the A-ring to obtain methyl olean-12-en-28-oate (5) [18].…”

mentioning

confidence: 99%

“…for 2 min at À 788. Then, Me 2 S (1 ml) was added, and the mixture was maintained at r.t. during 12 h with stirring, evaporated to dryness, and purified over SiO 2 to give 23 (12 mg, 24%), methyl (1aS,3aS,7aR,7bR)-octahydro-1a,6,6-trimethyl-7b-(2-oxoethyl)naphtho[1,2-b]oxirene-3a(1aH)-carboxylate (24, 10 mg, 32%) [18], and [(2S,4aS,8aR)-hexahydro-2-hydroxy-2,7,7-trimethyl-9-oxo-2H-1,4a-(epoxymethano)naphthalen-1(5H) (1R,2R,4aS,8aS)-Octahydro-5,5,8a-trimethyl-1H-spiro[naphthalene-2,2'-oxiran]-1-ol (26). Compound 9 (100 mg, 0.22 mmol) was dissolved in AcOEt (8 ml), stirred at À 788, and an O 3 flow lower than 0.1 l/min (50% O 2 /50% O 3 ) was passed through the soln.…”

mentioning

confidence: 99%

“…was concentrated under reduced pressure. The solid residue was purified with SiO 2 CC to give 44 (49 mg, 98%) [18].…”

mentioning

confidence: 99%

See 4 more Smart Citations

Bioactive Compounds with Added Value Prepared from Terpenes Contained in Solid Wastes from the Olive Oil Industry

Parra¹,

López²,

Garcı́a-Granados³

2010

Chemistry & Biodiversity

View full text Add to dashboard Cite

Starting from solid wastes from two-phase olive-oil extraction, the pentacyclic triterpenes oleanolic acid and maslinic acid were isolated. These natural compounds were transformed into methyl olean-12-en-28-oate (5), which then was transformed into several seco-C-ring triterpene compounds by chemical and photolytic modifications. The triene seco-products were fragmented through several oxidative procedures to produce, simultaneously, cis- and trans-decalin derivatives, both potential synthons for bioactive compounds. The chemical behavior of the isolated fragments was investigated, and a suitable approach to several low-molecular-weight terpenes was performed. These are interesting processes for the value-addition to solid waste from the olive-oil industry.

show abstract

mentioning

confidence: 95%

mentioning

confidence: 99%

mentioning

confidence: 99%

mentioning

confidence: 99%

“…was concentrated under reduced pressure. The solid residue was purified with SiO 2 CC to give 44 (49 mg, 98%) [18].…”

mentioning

confidence: 99%

See 3 more Smart Citations

Bioactive Compounds with Added Value Prepared from Terpenes Contained in Solid Wastes from the Olive Oil Industry

Parra¹,

López²,

Garcı́a-Granados³

2010

Chemistry & Biodiversity

View full text Add to dashboard Cite

show abstract

Ruthenium(III) Chloride

McKinney

Che

Wong

et al. 2013

Encyclopedia of Reagents for Organic Synthesis

View full text Add to dashboard Cite

Synthesis of Novel 8,14‐Secoursane Derivatives: Key Intermediates for the Preparation of Chiral Decalin Synthons from Ursolic Acid

Zhang

Yang

et al. 2012

Helvetica Chimica Acta

View full text Add to dashboard Cite

The novel 8,14-secoursatriene derivative 6 was synthesized starting from ursolic acid (1) via methyl esterification of the 17-carboxylic acid group and benzoylation of the 3-hydroxy group (! 2; Scheme 1), ozone oxidation of the C(12)¼C(13) bond (! 3), dehydrogenation with Br 2 /HBr (! 4), enol acetylation of the resulting carbonyl group (! 5; Scheme 2), and ring-C opening with the aid of UV light (! 6). Ring-C-opened dienone derivative 7 of ursolic acid was also obtained via selective hydrolysis of 6 (Scheme 2). Both compounds 6 and 7 are key intermediates for the preparation of chiral decalin synthons from ursolic acid.

show abstract

Oxidation of several triterpenic diene and triene systems. Oxidative cleavage to obtain chiral intermediates for drimane and phenanthrene semi-synthesis

Cited by 20 publications

References 27 publications

Bioactive Compounds with Added Value Prepared from Terpenes Contained in Solid Wastes from the Olive Oil Industry

Bioactive Compounds with Added Value Prepared from Terpenes Contained in Solid Wastes from the Olive Oil Industry

Ruthenium(III) Chloride

Synthesis of Novel 8,14‐Secoursane Derivatives: Key Intermediates for the Preparation of Chiral Decalin Synthons from Ursolic Acid

Contact Info

Product

Resources

About