ABSTRACT
A new synthetic strategy toward puupehenone-related bioactive metabolites from sclareol oxide, based on a Diels-Alder cycloaddition approach, is described. Utilizing this, marine ent-chromazonarol and the potent angiogenesis inhibitor 8-epipuupehedione have been synthesized.
Subject(s)
Angiogenesis Inhibitors/chemical synthesis , Chemistry, Organic/methods , Sesquiterpenes/metabolism , Terpenes/chemical synthesis , Xanthones/metabolism , Angiogenesis Inhibitors/chemistry , Sesquiterpenes/chemistry , Terpenes/chemistry , Xanthenes/chemical synthesis , Xanthones/chemistryABSTRACT
[reaction: see text] A new route toward puupehenone-related bioactive metabolites from (-)-sclareol, based on the palladium(II)-mediated diastereoselective cyclization of a drimenylphenol, is described. Utilizing this, the first enantiospecific synthesis of the antitumor and antimalarial (-)-15-oxopuupehenol, together with improved syntheses of (+)-puupehenone, (+)-puupehedione, and (+)-15-cyanopuupehenone, were accomplished.
Subject(s)
Antimalarials/chemical synthesis , Antineoplastic Agents/chemical synthesis , Diterpenes/chemistry , Diterpenes/chemical synthesis , Sesquiterpenes/chemistry , Xanthones/chemistry , Animals , Antimalarials/chemistry , Antineoplastic Agents/chemistry , Molecular Structure , Porifera/chemistry , Sesquiterpenes/chemical synthesis , Stereoisomerism , Xanthones/chemical synthesisABSTRACT
[structure: see text]. The tetracyclic ketal 24, a suitable intermediate for the synthesis of antitumor pentacyclic quassinoids, has been efficiently prepared from communic acids (5a-c), via methyl ketone 9. The synthetic sequence from 9 to 24 consists of 15 steps in 12% overall yield.
Subject(s)
Antineoplastic Agents, Phytogenic/chemical synthesis , Diterpenes/chemical synthesis , Quassins , Plants, Medicinal/chemistry , TerpenesABSTRACT
The neutral fraction of the hexane extract of the aerial parts of Santolina viscosa afforded eight new longipinene derivatives (1-8), oblongifolidiol (9), and several other known compounds. The structures of 1-8 were established by spectroscopic methods and chemical transformations. The vulgarone A-type structure previously reported for oblongifolidiol has been reassigned as the longipinene derivative 9 using 2D NMR, chemical correlations, and X-ray diffraction.
Subject(s)
Plants, Medicinal/chemistry , Sesquiterpenes/chemistry , Magnetic Resonance Spectroscopy , Morocco , Sesquiterpenes/isolation & purification , Spain , Spectrophotometry, Infrared , X-Ray DiffractionABSTRACT
The hexane extract of aerial parts of Santolina rosmarinifolia subsp. canescens afforded eight new sesquiterpenes in addition to known compounds. Their structures were determined by spectroscopic methods and chemical transformations. The conformational analysis of the germacrane constituents was carried out by spectroscopic methods, including NMR at varying temperature and by molecular mechanics calculations. The antifeedant, antibacterial and antitumoral activity of selected compounds has been tested.
