A biomimetic approach to some specifically functionalized cyclic terpenoids

• Autorzy: Kulcitki V.
• Języki publikacji: EN

Abstrakty

EN

The paper relates on the current advancements in the synthesis of complex cyclic terpenoids by superacidic induced cyclization of open chain precursors. It is shown that functional groups disposal in the initial substrate strongly influences the reaction outcome. Possible variations of the investigated compound structures include particularly α-functionalization and α,ω-bifunctionalization. This approach allowed a selective initiation of cyclization sequence from an internal double bond or suspending the ring closure cascade to partially cyclized compounds. The reported synthetic schemes are attempts to mimic the biogenetical processes postulated in the living systems.

Słowa kluczowe

PL

isoprenoid; terpenoid; cyclization; cyclic terpenoid; enzymatic catalysis; chemical catalysis; superacidic cyclization; polycyclic system

• Wydawca: -
• Czasopismo: Acta Biochimica Polonica
• Rocznik: 2007
• Tom: 54
• Numer: 4
• Opis fizyczny: p.679-693,fig.,ref.

Twórcy

autor

Kulcitki V.

• Institutul de Chimie al ASM, str.Academiei, 3, MD-2028, Chisinau, Republica Moldova

Bibliografia

• Armstrong RJ, Harris FL, Weiler L (1982) Electrophilic cyclization of polyene allylsilanes. Synthesis of albicanyl acetate. Can J Chem 60: 673-675.
• Asakawa Y (1995) Chemical constituents of the bryophytes. In Progress in the Chemistry of Organic Natural Products. Herz W, Kirby WB, Moore RE, Steglich W, Tamm Ch, eds. 65: pp 1-618. Springer, Vienna.
• Asakawa Y (2001) Recent advances in phytochemistry of bryophytes-acetogenins, terpenoids and bis(bibenzyl)s from selected Japanese, Taiwanese, New Zealand, Argentinean and European liverworts. Phytochemistry 56: 297-312.
• Asakawa Y (2004) Chemosystematics of the Hepaticae. Phytochemistry 65: 623-669.
• Bartlett PA (1984) In Asymmetric Synthesis. Morrison JD, ed, 3: pp 341-409. Academic Press, New York.
• Brunoldi E, Luparia M, Porta A, Zanoni G, Vidari G (2006) Biomimetic cyclizations of functionalized isoprenoid polyenes: cornucopia of synthetic opportunities. Curr Org Chem 10: 2259-2282.
• De Carvalho MS, Jacobs RS (1991) Two-step inactivation of bee venom phospholipase A2 by scalaradial. Biochem Pharmacol 42: 1621-1627.
• Cimino G, De Stefano S, Minale L (1974) Scalaradial, a third sesterterpene with the tetracarbocyclic skeleton of scalarin, from the sponge Cacospongia mollior. Experientia 30: 846-847.
• Cimino G, Sodano G, Spinella A (1987) Correlation of the reactivity of 1,4-dialdehydes with methylamine in biomimetic conditions to their hot taste covalent binding to primary amines as a molecular mechanism in hot taste covalent receptors. Tetrahedron 43: 5401-5410.
• Della Monica C, Della Sala G, Izzo I, De Petrocellis L, di Marzo V, Spinella A (2007) Enantioselective synthesis of 1-(R)-hydroxypolygodial and its 9α epimer, 1-(R)-hydroxyisotadeonal. Tetrahedron 63: 6866-6873.
• Feld H, Hertewich UM, Zapp J, Becker H (2005) Sacculatane diterpenoids from axenic cultures of the liverwort Fossombronia wondraczekii. Phytochemistry 66: 1094-1099.
• Gavriliuk OA, Korchagina DV, Osadchii SA, Barkhash BA (1988) Cyclization of acyclic isoprenoids. IV. Ring closure with the formation of C2-oxygen atom bond. Zhurnal Org Khim (Journal of Organic Chemistry, Russian) 5: 966.
• Grinco M, Kulcitki V, Ungur N, Jankowski W, Chojnacki T, Vlad PF (2007a) Superacid-catalyzed cyclization of methyl (6Z)-geranylfarnesoates. Helv Chim Acta 90: 1223-1229.
• Grinco M, Kulcitki V, Ungur N, Barba A, Deleanu C, Vlad P (2007b) Synthesis of 16-hydroxygeranylgeraniol and its derivatives from geraniol. Khim Prirod Soed (Chemistry of Natural Compounds, Russian) 43: 277-281.
• Grosjean E, Poinsot J, Charrie-Duhaut A, Tabuteau S, Adam P, Trendel J, Schaeffer P, Connan J, Dessort D, Albrecht P (2001) Synthesis and NMR characterization of novel highly cyclized polyprenoid hydrocarbons. J Chem Soc Perkin Trans 1 711-719.
• Hagiwara H, Uda H (1988) Total synthesis of (+)-dysideapalaunic acid. J Chem Soc Chem Commun 815-817.
• Hagiwara H, Uda H (1989) A total synthesis of (-)-sacculatal. Bull Chem Soc Jpn 62: 624-626.
• Hagiwara H, Uda H (1990) Total synthesis of (+)-perrottetianal. J Chem Soc Perkin Trans 1 1901-1908. Hagiwara H, Uda H (1991) Total synthesis and absolute stereostructure of (+)-dysideapalaunic acid. J Chem Soc Perkin Trans 1 1803-1807.
• He H, Kulanthaivel P, Baker BJ (1994) New cytotoxic sesterterpenes from the marine sponge Spongia sp. Tetrahedron Lett 35: 7189-7192.
• Jaki B, Heilmann J, Sticher O (2000) New antibacterial metabolites from the cyanobacterium Nostoc commune (EAWAG 122b). J Nat Prod 63: 1283-1285.
• Jansen BJM, de Groot A (2004) Occurrence, biological activity and synthesis of drimane sesquiterpenoids. Nat Prod Rep 21: 449-477.
• Jaquesy JC (1997) Natural product chemistry in superacids. In Stable carbocation chemistry. Prakash SGK, Schleyer PVR, eds, pp 549-574. John Wiley&Sons, New York.
• Kamo T, Sato K, Seri K, Shibata H, Hirota M (2004) Geranylgeraniol-type diterpenoids, Boletinins A-J, from Boletinus cavipes as inhibitors of superoxide anion generation in macrophage cells. J Nat Prod 67: 958-963.
• Kamaya R, Masuda K, Suzuki K, Ageta H, Hsu H-Y (1996) Fern constituents. Sesterterpenoids isolated from fronds of Aleuritopteris mexicana. Chem Pharm Bull 44: 690-694.
• Kernan MR, Faulkner DJ, Parkanyi L, Clardy J, De Carvalho MS, Jacobs RS (1989) Luffolide, a novel anti-inflammatory terpene from the sponge Luffariella sp. Experientia 45: 388-390.
• Korchagina DV, Gavriliuk OA, Barkhash VA, Vlad PF, Ungur N, Popa N (1993) Isomerisation of 6,7-epoxygeranylacetate in superacids. Zhurnal Org Khim (Journal of Organic Chemistry, Russian) 2: 323-325.
• Kulcitki V, Ungur N, Vlad P (1998) Superacidic cyclization of terpenic phenylsulfones. Tetrahedron 54: 11925-11934.
• Kulcitki V, Ungur N, Deleanu C, Vlad PF (1999) Superacidic cyclization of ω-oxygeraniol diacetate and benzyl ether of ω-acetoxygeraniol. Russ Chem Bull 1: 135-137.
• Kulcitki V, Ungur N, Vlad P, Gavagnin M, Castelluccio F, Cimino G (2000) Superacidic cyclization of all-trans-ω-acetoxyfarnesyl benzyl ether. Synthesis 3: 407-410.
• Kumar SK, Amador M, Hidalgo M, Bhatb SV, Khan SR (2005) Design, synthesis and biological evaluation of novel riccardiphenol analogs. Bioorg Med Chem 13: 2873-2880.
• Kurbanov M, Semenovskii AV, Smit VA (1973) Cyclization of isoprenoid compounds. Communication 27. Fluorosulfonic acid - a new perspective cyclization agent. Izv Acad Nauk USSR, Ser Khim 2: 390 (in Russian).
• Lan WJ, Li HJ (2007) New sesterterpenoids from the marine sponge Phyllospongia papyracea. Helv Chimica Acta 90: 1218-1222.
• Malheiros A, Cechinel Filho V, Schmitt CB, Yunes RA, Escalante A, Svetaz L, Zacchino S, Delle Monache F (2005) Antifungal activity of drimane sesquiterpenes from Drimys brasiliensis using bioassay-guided fractionation. J Pharm Pharm Sci 8: 335-339.
• Perry NB, Foster LM (1995) Sesquiterpenequinol from a New Zealand liverwort, Riccardia crassa. J Nat Prod 58: 1131-1135.
• Polovinka MP, Korchagina DV, Gatilov YuV, Bagrianskaya IYu, Barkhash VA, Shcherbukhin VV, Zefirov NS, Perutsky VB, Ungur ND, Vlad PF (1994) Cyclization and rearrangements of farnesol and nerolidol stereoisomers in superacids. J Org Chem 59: 1509-1517.
• Potts BCM, Faulkner DJ, De Carvalho MS, Jacobs RS (1992) Chemical mechanism of inactivation of bee venom phospholipase A2 by the marine natural products manoalide, luffariellolide, and scalaradial. J Am Chem Soc 114: 5093-5100.
• Renoux J-M, Rohmer M (1986) Enzymatic cyclization of all-trans pentaprenyl and hexaprenyl methyl ethers by a cell-free system from the protozoon Tetrahymena pyriformis. The biosynthesis of scalarane and polycyclohexaprenyl derivatives. Eur J Biochem 155: 125-132.
• Schaeffer P, Poinsot J, Hauke V, Adam P, Wehrung P, Trendel JM, Albrecht P, Dessort D, Connan J (1994) Novel optically active hydrocarbons in sediments: evidence for an extensive biological cyclization of higher regular polyprenols. Angew Chem Int Ed Engl 33: 1166-1169.
• Sutherland JK (1991) Polyene cyclizations. In Comprehensive organic syntheses. Trost BM, Fleming I, eds, 3: pp 341-377. Pergamon Press, New York.
• Swiezewska E, Sasak W, Mankowski T, Jankowski W, Vogtman T, Krajewska I, Hertel J, Skoczylas E, Chojnacki T (1994) The search for plant polyprenols. Acta Biochim Polon 41: 221-260.
• Tori M, Hamaguchi T, Sagawa K, Sono M, Asakawa Y (1996) Total synthesis and absolute configuration of riccardiphenols A and B, isolated from the liverwort Riccardia crassa. J Org Chem 61: 5362-5370.
• Torre MC, Sierra MA (2004) Comments on recent achievements in biomimetic organic synthesis. Angew Chem Int Ed Engl 43: 160-181
• Ungur N, Kulcitki V (2007) Occurrence, biological activity and synthesis of cheilanthane sesterterpenoids. In preparation.
• Ungur N, Popa N, Vlad PF (1993a) Interaction of 6,7-epoxygeranylacetate and 10,11-epoxyfarnesylacetate with fluorosulfonic acid. Khim Prirod Soed (Chemistry of Natural Compounds, Russian) 5: 691-697.
• Ungur N, Popa N, Kulcitki V, Vlad PF (1993b) Interaction of terminal epoxides of α-geranyl and α-farnesylacetate with fluorosulfonic acid. Khim Prirod Soed (Chemistry of Natural Compounds, Russian) 5: 697-701.
• Ungur N, Kulcitki V, Gavagnin M, Castelluccio F, Vlad PF, Cimino G (2002) Studies towards the synthesis of cheilanthane sesterterpenoids: superacidic cyclisation of methyl 13Z, 17Z- and 13Z, 17E-bicyclogeranylfarnesoates. Tetrahedron 58: 10159-10165.
• Van Tamelen EE (1968) Bioorganic chemistry: sterols and acyclic terpene terminal epoxides. Acc Chem Res 1: 111.
• Van Tamelen EE, McCormic JP (1969) Terpene terminal epoxides. Mechanistic aspects of conversion to the bicyclic level. J Am Chem Soc 91: 1847-1848.
• Van Tamelen EE, Storni A, Hessler EJ, Schwartz MA (1982) Cyclization studies with (+)-10,11-oxidofarnesyl acetate, methyl farnesate and (+)-10,11'-oxido-farnesate. Bioorg Chem 11: 133.
• Vlad PF (1993) Superacidic cyclization of terpenoids. Pure Appl Chem 6: 1329-1336