Reactivity of Chiral Sesquiterpene Synthons Obtained by the Degradation of Maslinic Acid from Olive‐Pressing Residues

References

• Manna , S. , Yadagiri , P. and Falck , J. R. 1987 . Terpenoid precursors via steroid degradation: Synthesis of (−)‐warburganal . J. Chem. Soc., Chem Commun. , : 1324 – 1325 .
   Google Scholar
• Urones , J. G. , Marcos , I. S. , Gómez‐Pérez , B. , Díez , D. , Lithgow , A. M. , Gómez , P. M. , Basabe , P. and Garrido , N. M. 1994 . Diasteroselective ring‐opening of 12‐acetoxy‐9α and 9β(11)‐epoxy‐7‐drimene: Homochiral semisynthesis of polygodial and warburganal . Tetrahedron , 50 : 10995 – 11012 .
   Web of Science ®Google Scholar
• Barrero , A. F. , Alvarez‐Manzaneda , E. J. and Chahboun , R. 1998 . Synthesis of wiedendiol‐A and wiedendiol‐B from labdane diterpenes . Tetrahedron , 54 : 5635 – 5650 .
   Web of Science ®Google Scholar
• Bolster , M. G. , Lagnel , B. M. F. , Jansen , B. J. M. , Morin , C. and de Groot , A. 2001 . The synthesis of Ambrox‐like compounds starting from (+)‐larixol . Tetrahedron , 57 : 8369 – 8379 . Part 2
   Web of Science ®Google Scholar
• 1996 . Dictionary of Natural Products on CD‐ROM, ver. 5.1; Chapman & Hall
   Google Scholar
• Garcia‐Granados , A. , Martinez , A. , Parra , A. and Rivas , F. 1998 . Process for the industrial recovery of oleanolic and maslinic acids contained in the olive milling byproducts . PCT Int. Appl. W0 98 04331; Chem Abstr. , 128 : 179706
   Google Scholar
• Kashiwada , Y. , Ikeshiro , Y. , Nagao , T. , Okabe , H. , Consentino , L. M. and Lee , K. H. 2000 . Anti‐AIDS agents 38: Anti‐HIV activity of 3‐O‐acylursolic acid derivatives . J. Nat. Prod. , 63 : 1619 – 1622 .
   PubMed Web of Science ®Google Scholar
• Mengoni , F. , Lichtner , M. , Battinelli , L. , Marzi , M. , Mastoianni , C. M. , Vullo , V. and Mazzanti , G. 2002 . In vitro anti‐HIV activity of oleanolic acid on infected human mononuclear cells . Planta Med. , 68 : 111 – 114 .
   PubMed Web of Science ®Google Scholar
• Honda , T. , Rounds , B. V. , Bore , L. , Finlay , H. J. , Favaloro , F. G. Jr. , Suh , N. , Wang , Y. , Sporn , M. B. and Gribble , G. W. 2000 . Synthetic oleanane and ursane triterpenoids with modified rings A and C: A series of highly active inhibitors of nitric oxide production in mouse macrophages . J. Med. Chem. , 43 : 4233 – 4246 .
   PubMed Web of Science ®Google Scholar
• Garcia‐Granados , A. , Lopez , P. E. , Melguizo , E. , Moliz , J. N. , Parra , A. and Simeo , Y. 2003 . Epoxides, cyclic sulfites and sulfates from natural pentacyclic triterpenoids: Theoretical calculations and chemical transformations . J. Org. Chem. , 68 : 4833 – 4844 .
   PubMedGoogle Scholar
• Garcia‐Granados , A. , Lopez , P. E. , Melguizo , E. , Parra , A. and Simeo , Y. 2004 . Partial synthesis of C‐ring derivatives from oleanolic and maslinic acids: Formation of several triene systems by chemical and photochemical isomerization processes . Tetrahedron , 60 : 1491 – 1503 .
   Google Scholar
• Garcia‐Granados , A. , Lopez , P. E. , Melguizo , E. , Parra , A. and Simeo , Y. 2004 . Oxidation of several triterpenic diene and triene systems: Oxidative cleavage to obtain quiral intermediates for drimane and phenantrene semisynthesis . Tetrahedron , 60 : 3831 – 3845 .
   Google Scholar
• Liu , H. J. and Tran , D. D. P. 1999 . Intramolecular Friedel–Crafts alkylation promoted by the cross conjugated β‐keto ester system: An efficient approach to highly functionalized hydrophenanthrenes and hydrochrysenes . Tetrahedron Lett. , 40 : 3827 – 3830 .
   Web of Science ®Google Scholar
• Paredes , E. , Biolatto , B. , Kneeteman , M. and Mancina , P. 2002 . One‐step synthesis of 2,9‐disubstituted phenanthrenes via Diels–Alder reactions using 1,4‐disubstituted naphthalenes as dienophiles . Tetrahedron Lett. , 43 : 4601 – 4603 .
   Google Scholar
• Kraus , G. A. , Hoover , K. and Zhang , N. 2002 . Synthesis of phenanthrenes from formylbenzoquinone . Tetrahedron Lett. , 43 : 5319 – 5321 .
   Google Scholar
• Barrero , A. F. , Alvarez‐Manzaneda , E. , Alvarez‐Manzaneda , R. , Arseniyadis , S. and Guittet , E. 1990 . Achilleol B: A new tricyclic triterpene skeleton from Achillea odorata L. . Tetrahedron , 46 : 8161 – 8168 .
   Web of Science ®Google Scholar
• Akihisa , T. , Arai , K. , Kimura , Y. , Koike , K. , Kokke , W. C. M. C. , Shibata , T. and Nikaido , T. 1999 . Camelliols A‐C, three novel incompletely cyclized triterpene alcohols from sasanqua oil (Camellia sasanqua) . J. Nat. Prod. , 62 : 265 – 268 .
   PubMed Web of Science ®Google Scholar
• Jansen , B. J. M. and De Groot , A. 1991 . The synthesis of drimane sesquiterpenoids . Nat. Prod. Rep. , 8 : 319 – 337 . and references cited therein
   Web of Science ®Google Scholar
• Kulcitki , V. , Ungur , N. , Gavagnin , M. , Carbone , M. and Cimino , G. 2004 . Synthesis and absolute stereochemistry of marine nor‐sesquiterpene austrodoric acid . Tetrahedron: Asymmetry , 15 : 423 – 428 .
   Google Scholar
• Gansäuer , A. and Rinker , B. 2002 . A comparison of electron transfer reagents in the reductive opening of epoxides: Reasons for the superiority of titanocene based complexes . Tetrahedron , 58 : 7017 – 7026 .
   Google Scholar