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Lignan Natural Products Baran Group Meeting November 18, 2005 Mike Demartino Lignan Natural Products Baran Group Meeting November 18, 2005 Mike DeMartino -Classification of lignan natural products: -Biosynthesis: Ar O -This topic nicely bridges two other Baran Group meeting topics, meaning Ar OH Ar O O O Ar that these will not be detailed in this lecture. In the most general sense, Ar' OH Ar' O Ar' the biosynthesis if lignans can be thought of as such: Ar' dibenzylbutan(diol)e tetrahydrofuran tetrahydrofuran dibenzylbutyrolactone Carbohydrates --> Shikimic acid pathway --> Aromatic a.a.'s --> Cinnamic acids --> Lignans (Steganes) OH OH O O RO See Group Meeting: See Group Meeting: Ambhaikar, (2005) Zografos, (2004) RO O O RO O http://www.scripps.edu/chem/baran/html/meetingschedule.html O R'O Ar Ar CO2H CO2H tetralin naphthalene dibenzocyclooctadiene NH2 (stegane) cinnamic -Provisional statement acid Lignans are an extremely large class of natural products; for reasons detailed below, this lecture will focus on (bio)synthesis. That said, L-Phe O2 Shikimic NADPH neolignans (see next page) will not be discussed in detail. This is not Acid meant to give a comprehensive coverage of all synthetic routes to CO2H CO2H CO2H CO2H CO2H CO2H lignans, but rather a representitive sampling thereof. NH 2 O O 2 SAM 2 -Pharmacological properties NADPH NADPH SAM Because of the high structural diversity of this class of natural HO MeO MeO OH MeO OMe products, there is obviously an extraordinary range of medicinal OH OH OH OH OH OH properties and this area continues to be a fruitful research topic. L-Tyr 4-coumaric acid caffeic ferulic sinapic Many lignan containing plants have been used for centuries, (p-coumaric acid) acid acid acid particualrly in Asian communities, as cures and remedies for various ailments. This subject will not be further elaborated upon as the sheer magnitude of the topic warrants more than this particualr avenue of OH OH OH discussion. For interesting case studies on some of the more prolific medicinally relavant lignans, see Ref 1 below. Ref 5 also has execllent discussions on the bioactivites of plant lignans. -Key References MeO MeO OMe 1. Ayres, D.C., Loike, J.D. In Lignans Chemical, Biological, and Clinical Properties; OH OH OH 4-hydroxycinnamyl alcohol coniferyl sinapyl Cambridge University Press: Cambridge, 1990. (p-coumaryl alcohol) alcohol alcohol 2. Dewick, P.M. Medicinal Natural Products, 2nd Ed.; John Wiley & Sons, LTD, W. Sussex, 2002. Polymers 3. Barton, D., Nakanishi, K. Comprehensive Natural Products Chemistry, Vol 3, x 2 x n PergamonPress. 4. Lewis, N.G. et. al. Phytochemical Reviews 2003, 2, 257. Lignans Lignin 5. Muhammad, S. et. al. Nat. Prod. Rep. 2005, ASAP. Lignan Natural Products Baran Group Meeting November 18, 2005 Mike DeMartino Lignins vs. Lignans -One-electron oxidation followed by free radical resonance Ar distribution, leads to oxidative phenol coupling products Ar OH O Ar' OH Ar' OH OH OH OH OH dibenzylbutan(diol)e tetrahydrofuran peroxidases Ar O + Ar –H O O O Ar' –e- Ar' tetrahydrofuran dibenzylbutyrolactone MeO MeO MeO MeO MeO OH OH O O OH O O O O RO O RO O coniferyl alcohol C2-C2 Ar Ar NEOLIGNANS LIGNANS [O] coup. tetralin naphthalene radical pairing in any fasion H+ RO (excluding C2-C2); can also O O be classified as lignans O OMe R'O OH O dibenzocyclooctadiene (stegane) OH Picture taken from: http://honeybee.helsinki.fi/MMSBL/Gerberalab/lignin_structure_gosta.html H H OMe quinonemethide intenal quench -Related because they are made up of the same starting materials; outside of the O synthetic literature, it is difficult to find one term without the other. HO HO (+)-pinoresinol MeO -Lignin is a complex aromatic biopolymer formed of hydroxycinnamyl alcohols, which MeO are connected to each other with various linkages . It is three-dimensional in structure likely occurs through O and is formed between other constituents of the cell wall, having covalent linkages to quinonemethide/ NADPH H+ reduction cellulose, hemicelluloses and proteins. Lignans (and neolignans) are dimers of hydroxy cinnamyl alcohols. OH MeO OH O -The most important function of lignin is to strengthen the cell walls of plants; lignan H H OMe NAD+ HO function in plants not well understood. O lactonization HO -Lignin is the 2nd most abundant source of organic material on the earth (cellulose). HO (–)-secoisolariciresinol MeO matairesinol MeO Note: ortho- -Lignin has no ordered, repeating structure, but has secondary structure. hydroxymethylether is the OH biogenic precursor to the aryl methylenedioxy moiety -Lignin is racemic, or mosty racemic, polymer on the order of 10K Daltons; lignans are OH modifications always chiral owing to a stereocontrolled oxidative coupling. O O O O O O -Still not much known with regards to the assemblage process of lignin; significantly O O cyclization O more about lignans is known. through O O O hydroxylation quinone- -Monomeric constitution of lignin highly dependant on specific plant, but mostly methide p-coumaryl, coniferyl, and sinapyl alcohols. MeO OMe MeO OMe MeO OMe OH podophyllotoxin OH desoxypodophyllotoxin OH yatein -Lignans are differrentiated after oxidative coupling. Lignan Natural Products Baran Group Meeting November 18, 2005 Mike DeMartino Ar OH Ar -Synthesis of dibenzylbutan(diol)e lignans -Synthesis of tetrahydrofuran O Ar' OH Ar' lignans 1. Ar'CH MgCl, Br 2 Ar NiCl (dppp) Me ArCH2ZnBr 2 Ar Pd(PPh3)4 O ONa 2. Raney Ni Ar' MeO OMe Br Br Me S Me Me O O MeO OMe Br S MeO MeO Me Me Me Me 1. ArMgBr OMe OMe 1. MeMgBr Pd(PPh ) Me NiCl (dppp) 3 4 Ar 2 Pd/C 2. Br2, AcOH Br 2. Ar'MgCl, Ar' S Br Me H2 NiCl2(dppp) low cat. 3. Raney Ni loading 60% Kumada, M., et. al. Tetrahedron Letters 1980, 21, 4017. MeO OMe O MeO OMe Me Me veraguensin Biftu, T., et. al. J. Chem. Soc. Perk. Trans. 1 1978, 1147. O ONa MeO OMe Me Me O O 1. Ac2O, Et3N, 98% O MeO OMe 2. NaH, Br O 1. (Me)2NH O MeO MeO OH (OEt) POCH CO Et B 7% BnO O 2 2 2 n O OMe OMe Me Me OH 83% 2. Swern; HO NMe2 Pd/C O 3. H2SO4, MeOH, 90% O ArMgBr O OH H2 OH 4. Pd/C, H2, 97% 68% high cat. 5. Ag2O, BnBr, 81% loading ~50% TsOH 69% MeO OMe O O MeO OMe O 1. Dibal OBn 2. Et3SiH 1. LHMDS; O Me Me HO BF3•Et2O O piperonal 64% 91% TBSO dihydroguaiaretic acid O O O 3. Pd (black) 2. TBSOTf O Biftu, T., et. al. J. Chem. Soc. Perk. Trans. 1 1978, 1147. HCO H 2,6-lut. O 4-epidihydrosesamin 2 O 60% OBn 93% O O *Note* This class have certainly been made many other different ways, but these are all O en route to higher oxidation state lignan natural products. O Yoda, H.T., et. al. Synlett 2001, 400. Lignan Natural Products Baran Group Meeting November 18, 2005 Mike DeMartino Ar PhS SPh OMe -Synthesis of tetrahydrofuran lignans (cont.) O MeO OH Ar' n-BuLi PhS SPh H ArCHO OMe *MenthO O MeO Me2 MeO O OH Si 62% O 1. Allyldimethyl O OMe *MenthO O chlorosilane ArCHO FMe2Si Et3N BF3•Et2O 1. HgO, O BF3•Et2O 2. LAH 2. Grubbs I dr = 9:1 THF/H2O 67% O O 73% Ar 89% O OMe O OMe O MeO OH HO BF3•Et2O O O OMe 1. OsO (cat) MeO H H OMe 4 44% MeO HO O NMO O 2. NaIO O HO OH 4 MeO (–)-eudesmin O 3. NaBH4 O 93% O O Feringa, B.L., et. al. J. Org. Chem. 1994, 59, 5999. O 4-epidihydrosesamin O O Miles, S.M., et. al. J. Org. Chem. 2004, 69, 6874. O OH 1. ArCHO ArCH(Cl)OMe Ar ZnCl2, Et3N Et3N O OMe O O O -Synthesis of furofuran lignans O O O 2. BH3•DMS O 58% 60% Recent review: Brown, R.C.D., et. al. Syn. 2004, 6, 811. O Ar' O O O HO O OH O C. fumago O air LDA, H H OMe TMSCl MeO O ~5% O 92% OMe O pinoresinol O HO H H O OH O O O O Pare, P.W., et. al. Tetrahedron Letters 1994, 35, 4731 O aptosimon TMSOTf OMe O Et N O OH O 3 O OMe OH O H H dr = 1.4:1 FeCl3, O2 O O Ar O O O 47% aq. ROH; 1. LAH O OMe O OTMS H H MeO H H O O O H SO 2. 220°C asarinin LAH; H H 2 4 O O 73% Ar O O 0.05 Torr. O HCl, MeO OMe O HO MeOH O O OH syringaresinol 62% O MeO Freudenberg, K., et. al. Chem. Ber. 1955, 88, 16. Whiting, D.A., et. al. J. Chem. Soc., Chem. Comm. 1984, 59, 590. Lignan Natural Products Baran Group Meeting November 18, 2005 Mike DeMartino Ar MeO2C -Synthesis of furofuran lignans (cont.) O O LDA; O Br FVP ArCHO O 500°C Recent review: Brown, R.C.D., et. al. Syn. 2004, 6, 811. Ar' CO Me O O 2 70% 0.04 mbar O CO2Me 66% O 1. LAH 98% 2. ArCH(OMe)2 O Ph TMSOTf, 55% SO2Ph O Ph Cl TMS TMS 1. CsF H H O O O Et SiH O 2. TBAF Ph O CsF 3 Ph O BF3•Et2O O 64% 18% O H H H H TMS Cl O O 70% OMe Ph O O O O O Hojo, M., et. al. Synlett 1996, 234. a-Ar: asarinin b-Ar: diasesamin a:b = 1:3 Steel, P.G.
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