Studies Toward the Total Synthesis of (±)-Noelaquinone
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1 Research Topic Seminar 18 June 2005 Studies Toward the Total Synthesis of (±)-Noelaquinone David Amantini WIPF GRUP The Role of Natural Products in Drug Discovery For thousands of years medicine and natural products have been closely linked through the use of traditional medicines and natural poisons. Which is the STATUS of NATURAL PRDUCTS in DRUG DISCVERY today? Butler, M. S. J. Nat. Prod David Wipf Group 1 6/20/2005
2 Understanding the Cell-Cycle with Natural Products Understanding Protein Function in Cells Genetic Approach: making mutations in genes that alter the function of the encoded protein Chemical Approach: to alter the function of the protein directly by using a cell - permeable ligand that binds to the protein in its intracellular environment Small molecule natural products inhibit progression of the cell cycle by binding to a protein required for cell division, thus helping to determine the function of the protein NATURAL PRDUCTS CEMISTRY CELL BILGY An understanding of cell cycle events helps in understanding the mechanisms of action of many cell - cycle inhibitors Currently the most valuable collection of ligands for use in the study of protein function are NATURAL PRDUCTS or compounds that are closely related to a NATURAL PRDUCT Schreiber, S. L. et al Chem. Biol Relative Timing of Arrest by Different Cell-Cycle Arrest Agents DISCDERMLIDE CN 2 Ac WRTMANNIN N RAPAMYCIN KADAIC ACID N AcN N N APIDICLIN TUNICAMYCIN V David Wipf Group 2 6/20/2005
3 The Viridin Family of Steroidal Antibiotic: The Furanosteroids Viridin Isolated in 1945 from Gliocadium Virens structure determined in 1966 Ac Isolated in 1957 from Penicillium Wortmannii and in1972 from Myrothecium Roridium, structure determined in 1972 Anti - Inflammatory Activity Antibiotic Activity Potent and Specific Phosphoinositide 3 - kinase (PI 3K) Inhibitors Viridiol Demethoxyviridin Demethoxyviridiol Wortmannolone Wipf, P. and alter, R. J. rg. Biomol. Chem Furanosteroids: Proposed Biosynthesis P P + Squalene P P Squalene 2,3-Epoxide Lanosterol Viridin Ac anson, J. R. Nat. Prod. Rep David Wipf Group 3 6/20/2005
4 Irreversible Inhibition of PI-3 Kinase Ac Ac N N2 (p110 PI-3 kinase)k802 (p110 PI-3 kinase)k802 Ac IC50 = 4.2 nm Ac IC50 = 4600 nm Ac Ac IC50 = 16.7 nm IC50 > 32,000 nm IC50 > 500 nm IC50 = 6.0 nm IC50 = 271 nm IC50 = 0.4 nm Norman, C. S. J. d. Chem Planar Polycyclics from the Marine Sponge Xestospongia Distribution of Marine Natural Products by Phylum Biogenetic rigins of Marine Natural Products David Wipf Group 4 6/20/2005
5 Planar Polycyclics from the Marine Sponge Xestospongia (+)-Xestoquinone (+)-alenaquinone (+)-alenaquinol Isolated from Xestospongia Sapra in 1960 Isolated from Xestospongia Exigua in 1983 Antibacterial Activity Cardiotonic Properties Inhibition of pp60 Kinase Inhibition of EGF Kinase Inhibition of the Dual Specificity Phosphatase Cdc25 Are These Compounds Triketides - Sesquiterpenes ybrids? Sesquiterpene Unit Triketide Unit Isozonarol (A Biosynthetic Link?) alenaquinone Protein Tyrosine Kinase (PTK) Inhibition IC 50 values against pp 60 (+)-Xestoquinone (+)-alenaquinone (+)-alenaquinol IC 50 = 60 µm IC 50 = 5 µm IC 50 = 0.6 µm Ac IC 50 >> 200 µm Viridin IC 50 = 30 µm IC 50 = 27 µm Crews, P. et al J. rg. Chem David Wipf Group 5 6/20/2005
6 Synthetic Efforts utline alenaquinone ARADA RDRIG SIBASAKI (Chiral building block) ( o-benzoquinone monoketals Cascade Reactions) (Catalytic Asymmetric Intramolecular Cascade eck-suzuki Couplings) Viridin SRENSEN (Alkyne Trimerization and p- Claisen Rearr.) SIBASAKI SIBASAKI Ac (Chiral building block) (Diastereoselective Intramolecular eck Couplings and Diosphenol Claisen) Synthesis of (±) - alenaquinol [Rodrigo] ( ) - alenaquinol 16 Steps 5 % arada, N. et al J. Am. Chem. Soc PhS + SPh PhI( 2 CCF 3 ) 2 NaC 3 SPh Trimethylbenzene 168 C + 36% SPh Toluene 120 C 94% SPh Na, TFA, DCM 97% SPh p-chloranil TiCl 4, Ac % CAN, - 2 Na 2 S 2 4, Acetone % ( ) - alenaquinol 10 steps 4% Rodrigo, R. G. A. et al J. rg. Chem David Wipf Group 6 6/20/2005
7 Synthesis of (+) - alenaquinol [Shibasaki] BBr 3, DCM BnBr, K 2 C 3 Cr 3 4. KMDS, I 5. 2, Pd/C 58% Tf 2 Py 99% Tf Tf TBDPS B Pd(Ac) 2 (S)-BINAP Toluene 120 C 20%, (85% ee) TBDPS TBAF NaB 4, 93% Tf 2 Py LDA, NaF NC 68% PTSA n-buli TIPSCl 96% TIPS NaI CuS 4 DDQ Ts, Acetone - 2 TIPS 2, Kt-Bu Pd 2 (dba) 3 CCl 3 4. TBAF 76% 58% CAN, - 2 Na 2 S 2 4, Acetone % ( ) - alenaquinol 21 steps 0.3% Shibasaki, M. et al J. rg. Chem Synthesis of (±) - Viridin [Sorensen] TBS n-buli / DMF Br Zn, gcl 2 K 2 C 3, 85% (4 diastereoisomers) TBS [RhCl(PPh 3 ) 3 ], Et 88% TBS (CCl) 2, DMS TBS TBS n-buli TESCl, Imid., DMAP 70% TES i-pr 2 EtN, Xylenes 140 C DDQ 83% TES Br CsF sitylene, 160 C 61% TBS TBS TBS Grubbs - II Se 2, Dioxane 57% Dess - Martin NaB 4, Et s 4, TMEDA 72% Triphosgene, Py PPTS, EVE 86% EE TBS Li TBSTf, 2,6-Lutidine NaMDS, Tf 4. TBAF 5. Dess - Martin 6. PPTS, 57% ( ) - Viridin 23 steps 5% Sorensen, E. J. et al Angew. Chem. Int. ed David Wipf Group 7 6/20/2005
8 [ 1 ] Synthesis of (±) - [Shibasaki] ydrocortisone Ac (+)- 35 steps 0.02 % Shibasaki, M. et al Tetrahedron. Lett Steps SEMCl 2,6-Lutidine SEM Pd(Ac) 2 C 2 (Racemic) 27% Tf 9-BBN Tf [PdCl 2 (dppf)] Bn I Bn 56% 65% Bn SEM dr = 18-1 CsF, DMF PDC, NaAc DIBAL- 4. TBSCl, Imid. 39% Bn TBS 4. s 4, NM LA I, Ag 2 Ac 2, DMAP, Py 38% TBS Ac Cr 3, 3,5-di-Pyrazole Tf, unig base DMD, PPTS, (CCl 2 ) 2, DMS Br K 2 C 3 44% TBS Ac Xylene, 200 C NaB 4, CeCl 3 C() 3, PPTS 67% Ac TBS Shibasaki, M. et al Angew. Chem. Int. Ed [ 2 ] Synthesis of (±) - [Shibasaki] TBS Ac 4. s 4, NM TBAI 4 K 2 C 3, TPAP, NM 44% TBS C(N 2 ) 3, DMF Phosphate Buffer p % TBS 2 S 4, K 2 C 3 1N Na PDC, NaAc 55% TBS (CCl) 2, DMS 75% TBS Et 2 N, DCM TBS Et 2 N 1N Cl 60% TBS F - TEA Ac 2, Py 31% Ac ( ) - 41 Steps 0.04% Bn SEM TBS I TIPS cat Pd(0) X TBS TIPS Shibasaki, M. et al Angew. Chem. Int. Ed David Wipf Group 8 6/20/2005
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