New Methods of Indole Formations and Applications in Total Synthesis
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1 ew Methods of Indole Formations and Applications in Total Synthesis Palladium-Catalyzed Synthesis of 2-(Aminomethyl)indoles from Ethyl 3-(o-Trifluoroacetamidophenyl)-1-Propargyl Carbonate Ilaria Ambrogio, Sandro Cacchi and Giancario Fabrizi Org. Lett., 2006, ASAP and A ew Modular Indole Synthesis. Construction of the Highly Strained CDEF Parent Tetracycle of odulisporic Acids A and B Amos B. Smith, III, László Kürti and Akin H. Davulcu Org. Lett., 2006, ASAP Erick B. Iezzi, PhD Current Literature May 6, 2006 Erick Wipf Group 1 5/10/2006
2 Why are these articles significant? ew routes to functionalized indoles: - significant for natural product and pharmaceutical drug synthesis Cacchi s group developed a simple approach to 2-(aminomethyl)indoles and the important class of 2-(piperazin-1-ylmethyl)indoles Smith s group developed a new synthesis of tetracyclic indoles via a Stille crosscoupling/buckwald-hartwig union/cyclization Erick Wipf Group 2 5/10/2006
3 Synthesis and Functionalization of Indoles Classical methods (over last 100 years): - Fisher synthesis - Gassman synthesis - Madelung cyclization - Bischler synthesis O Br + Bischler-Möhlau synthesis H 2 heat H Palladium-catalyzed syntheses (over last 40 years): - industrial synthesis of acetaldehyde from ethylene (PdCl 2 and CuCl 2 ) launched a new area of research - fewer steps, less waste, etc. Erick Wipf Group 3 5/10/2006
4 Alkyne-Based Palladium-Catalyzed Assembly of Indoles Mechanism Example Cacchi and Fabriz. Chem. Rev. 2005, 105, 2873 Erick Wipf Group 4 5/10/2006
5 Alkene-Based Palladium-Catalyzed Assembly of Indoles Mechanism Example Cacchi and Fabriz. Chem. Rev. 2005, 105, 2873 Erick Wipf Group 5 5/10/2006
6 Palladium-catalyzed hydroarylation/cyclization of alkynes (Cacchi s methodology) Used to construct heterocyclic rings: - butenolides - quinolines - chromenes - coumarins - chromanols OEt I OMe OMe TsOH (10%), EtOH/H 2 O (8:2), 2 h, rt, 87% OMe OTHP OEt Pd(OAc) 2 (5 mol%), DMF, KOOCH, 40 o C, 4 h, 66% OEt OEt OTHP CHO OTHP TsOH (10%), Me 2 CO/H 2 O (8:2), 24 h, rt, 86% O OH H OMe CrO 3, Me 2 CO/HCl 2 (8:2), 2.5 h, rt, 79% O O OMe Cacchi, et al. Synlett. 1997, 1367 Erick Wipf Group 6 5/10/2006
7 Palladium-Catalyzed Synthesis of 2-(Aminomethyl)indoles (Cacchi et al., ASAP) desired product * A new palladium-catalyzed cyclization of an acyclic alkyne to a free -H functionalized indole! interesting result Erick Wipf Group 7 5/10/2006
8 Synthesis of 2-(piperazin-1-ylmethyl)indoles (Cacchi et al., ASAP) 2 privileged structures (indole and piperazine nuclei) - significant components in pharmaceutical chemistry (i.e., Clozapine) - formed in a single step Two C- bonds formed in a single operation Stepwise pathways (2 & 3 positions) H Ph Ph Cl H Ar H aq. CH 2 O, CH 2 Cl 2 / AcOH (4:1), rt, 30 min. 50% H H R 2 H, DMF, 60 o C H Ar Gmeiner, et al. J. Med. Chem. 2000, 43, 4563 Erick Wipf Group 8 5/10/2006
9 Synthesis of Starting Materials and Evaluation of Conditions for 2-(Piperazin-1-ylmethyl)indole Formation I O O TFAA, THF, Et 3, 0 o C, 2 h O O p-tsoh, 40 o C, Acetone/H 2 O (1:1), 6 h H 2 PdCl 2 (PPh 3 ) 2, CuI, Et 2 H, DMF, 60 o C 12 h HCOCF 3 Ethyl chloroformate, CH 2 Cl 2, Et 3, 0 o C, 2 h 80% (4 steps) HCOCF 3 OCO 2 Et Erick Wipf Group 9 5/10/2006
10 Evaluation of Functional Groups in 2-(Piperazin-1-ylmethyl)indole Formations Erick Wipf Group 10 5/10/2006
11 Evaluation of Secondary Amines and Proposed Reaction Mechanism HCOCF 3 OCO 2 Et Amine, Pd cat. H or H R 2 X = C,O X Proposed mechanism ot acidic enough Erick Wipf Group 11 5/10/2006
12 A ew Modular Indole Synthesis. Construction of the Highly Strained CDEF Parent Tetracycle of odulisporic Acids A & B (Smith et al., ASAP) odulisporanes: - a novel class of indole diterpene alkaloids - display potent insecticidal properties (i.e., fleas and ticks) - modulation of the invertebrate-specific glutamate-gated chloride ion channels - odulisporic acid A first reported by Merck in 1997 as a lead compound (potentcy, stability and pharmacokinetic profile was not optimal!) Erick Wipf Group 12 5/10/2006
13 Attempts to Synthesize the CDE Core via Known Indole Formations (Smith et al., ASAP) Reported approaches to CDE tricycle Application of the Fisher Indole Synthesis High strain in five-membered system! Erick Wipf Group 13 5/10/2006
14 Stille Cross-Coupling/Buchwald-Hartwig Union/Cyclization Tactic (Smith et al., ASAP) o reaction with 2.5 mol% cat. Erick Wipf Group 14 5/10/2006
15 Preparation of a Highly Substituted and Strained Indole Derived from (+)-Estrone and Construction of Diverse Indoles Erick Wipf Group 15 5/10/2006
16 Summary of ew Indole Methodologies Cacchi s group developed a simple approach to 2-(aminomethyl)indoles and 2-(piperazin-1-ylmethyl)indoles under mild conditions in a single operation - high product yields - application to functionalized indoles Smith s group developed a new indole synthesis via a Stille/Hartwig-Buchwald coupling using mild conditions - application to structurally diverse indoles, especially novel tricyclic systems Erick Wipf Group 16 5/10/2006
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