Copper-Catalyzed Diastereoselective Arylation of Tryptophan Derivatives: Total Synthesis of (+)-
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1 Literature Report Copper-Catalyzed Diastereoselective Arylation of Tryptophan Derivatives: Total Synthesis of (+)- aseseazines A and B Reporter: Mu-Wang Chen Checker: Zhang-Pei Chen Date: Reisman, S. E. et al. J. Am. Chem. Soc. 2013, 135, California i Institute t of Technology 1
2 Contents 1 Pyrroloindoline 2 Synthesis of Aryl Pyrroloindolines via Friedel-Crafts-Type Arylation 3 Synthesis of faryl Pyrroloindolines li via Cu-Catalyzed C darylation 4 Summary
3 Pyrroloindoline Alkaloids S S Gliocladine C (1) R 2 R 1 aseseazine A (R 1 =,R 2 =) aseseazine B (R 1,R 2 =(C 2 ) 3 ) xidative cyclization reaction rganocatalyzed reaction Transition-metal-catalyzed reaction 3
4 Copper-Catalyzed Diastereoselective C3 Arylation-Cyclization
5 ptimization Studies (CuTf) 2 (10 mol%) ligand (22 mol%) [ o 2 I]X, C 2 Cl 2, 23 C 4a 5a entry ligand [ 2 I]X C3:C2 a dr a yield (%) a 1 - b [ 2 I]PF [ 2 I]PF 6 1:1 3: L1 [ 2 I]PF 6 1:1 3: L2 [ 2 I]PF 6 1:2 2:1 <5 5 L3 [ 2 I]PF 6 6:1 10: L4 [ 2 I]PF 6 12:1 12: L5 [ 2 I]PF 6 2:1 5: L6 [ 2 I]PF 6 1:11 4: L7 [ 2 I]PF 6 >20:1 >20:1 70 a Yield of major diastereomer was determined by 1 MR analysis of the crude reaction mixture. b o (CuTf) 2. was used. c Isolated yield
6 entry ligand [ 2 I]X C3:C2 a dr a yield (%) a 10 L8 [ 2 I]PF 6 1:1 4: L9 [ 2 I]PF 6 2:1 20: L7 [ 2 I]PF 4 >20:1 >20: L7 [ 2 I]AsF 6 >20:1 >20: L7 [ 2 I]Tf >20:1 >20:1 83 (85 c ) a Yield of major diastereomer was determined by 1 MR analysis of the crude reaction mixture. b o (CuTf) 2. was used. c Isolated yield 6
7 Substrate Scope of Pyrroloindoline Formation 4a-f R 1 R 2 s Cu Tf s (20 mol%) [Ar 1 -I-Ar 2 ]Tf, C 2 Cl 2,23 o C, 4-42 h Ar 1 5a-i R 2 R 1 5a 85% yield Bn 5b 66% yield 5b 50% yield 5d 64% yield 5e 51% yield 5f 71% yield b
8 Substrate Scope of Pyrroloindoline Formation a Reaction were conducted on a 0.3 mmol scale using symmetric [Ar 2 I]Tf, unless otherwise noted. Isolated yields are reported. b Ligand L6 (40 mol%) was used with [ 2 I]PF 6. c onsymmetric [Ar(p-xylyl)I]Tf was used.
9 Arylation of Tryptophan Carboxamide 7
10 Concise Total Syntheses of (+) aseseazine B 10
11 Concise Total Syntheses of (+) aseseazine A Br CF 3 (CuTf). 2 (10 mol%) L6 (40 mol%) 9, C 2 Cl 2,23 o C 5.3 mmol scale (59% yield) 4b 11 s I PF 6 1. ab 4, Et (92% yield) F 3 C 9 Br cat. Pd[P(o-tol) 3 ] 2 a 2 C 3,DMF,100 o C; then 1 Cl/ (56% yield) aseseazine A TES 10
12 Regioselective Arylative Dimerization of Diketopiperazine Alkaloids Movassaghi, M. et al. J. Am. Chem. Soc. 2011, 133,
13 Concise and Directed Syntheses of A and B 13
14 14
15 15
16 Enantioselective Copper-Catalyzed Construction of Aryl Pyrroloindolines via an Arylation Cyclization Cascade R PG 20 mol% Cat. + [siar]asf 6 ac 3, DCM -20 o C R PG Ar Cu Tf 98% yield >99% ee I Cu Tf s I Ar oxidative addition III Cu Ar -facial coordination R PG Ar Tf R III Cu PG -Cu(Box)Tf reductive elimination Tf Ar R PG - + Ar R PG MacMillan, D. W. C. et al. J. Am. Chem. Soc. 2012, 134,
17 A Copper-Catalyzed Arylation of Tryptamines for the Direct Synthesis of Aryl Pyrroloindolines Reisman, S. E. et al. Chem.Sci., 2012, 3,
18 Proposed Catalytic Cycle 18
19 Summary A Movassaghi and Kim (2011): Bromocyclization/Friedel-Crafts B MacMillan and Zhu (2012): Copper-Catalyzed, Enantioselective C3 Arylation-Cyclization C Reisman and Kieffer (2012): Copper-Catalyzed C3 Arylation-Cyclization 19
20 D Reisman and Kieffer (2012): Copper-Catalyzed, Diastereoselective C3 Arylation-Cyclization 20
21 The pyrroloindoline is a common structural motif that unites several biosynthetically distinct families of alkaloids. The prevalence of this indolederived heterocyclic framework continues to inspire the development of new reactions for its construction, and these efforts have delivered increasingly gy efficient total syntheses of biologically active natural products. Specifically, the development of tandem C3-functionalization/cyclization reactions of tryptamine and tryptophan derivatives has proven to be a particularly fruitful line of research. Such methods include a variety of oxidative cyclization reactions as well as recently discovered organocatalyzed and transitionmetal-catalyzed C C bond-forming processes. 21
22 In conclusion, a Cu-catalyzed site- and diastereoselective arylation of tryptophan derivatives has been developed. This reaction provides direct access to aryl pyrroloindolines under mild conditions with good functional group tolerance. Using this transformation to assemble the pyrroloindoline core enables the concise, stereoselective syntheses of the bisindole alkaloids (+)-naseseazines A and B in overall yields of 25 and 19%, respectively. The further development and application of this transformation in natural product synthesis is the subject of ongoing research in our laboratory. 22
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