A Concise Total Synthesis of (+)- Scholarisine A Empowered by a Unique C H ArylaBon
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1 A Concise Total Synthesis of (+)- Scholarisine A Empowered by a Unique C H ArylaBon Myles W. Smith and ScoO A. Snyder. J. Am. Chem. Soc., 2013, 135, Liming Cao Wipf Group Current Literature 9/21/2013 Liing Wipf Group Page 1 of 14 10/2/2013
2 Alstonia scholaris (L.) R. Br. Scholarisine A is an akuammiline alkaloid first isolated by Luo in 2007 from Alstonia scholaris (L.) R. Br. in the Yunnan province in China. The bark has been tradibonally used to treat gastrointesbnal condibons, malaria, cutaneous diseases, tumors, ulcers, chronic respiratory condibons (such as asthma and bronchibs), helminthiasis, and agalacba in India, China, Australia and Africa. The leaves have been historically used in dai ethnopharmacy to treat chronic respiratory diseases in Yunnan. The leaf extract, developed as a commercially available tradibonal Chinese medicine, has also been prescribed in hospitals and sold over the counter in drug stores. Org. Le , 10, 577 Integr. Cancer Ther. 2009, 8, 273 J. Ethnopharmacol. 2010, 129, 293 J. Ethnopharmacol. 2010,129, 174 Integr. Cancer Ther. 2010, 9, 261 A Modern Herbal (Vol. 1). New York, Dover PublicaBons, 1971, 29 Chin. J. Integr. Med Mar 28 hop:// Liing Wipf Group Page 2 of 14 10/2/2013
3 Scholarisine A The structure was elucidated by 1D and 2D NMR, FTIR, UV, and HRMS: - An indolenine fused to a strained carbocylic cage, adorned with terbary and quaternary stereocenters - PotenBally labile imine and bridging lactone funcbonal groups. Its biological properbes remain unexplored. Org. Le , 10, 577 J. Am. Chem. Soc., 2013, 135, Liing Wipf Group Page 3 of 14 10/2/2013
4 Smith s total synthesis of (+)- Scholarisine A J. Am. Chem. Soc. 2012, 134, 4037 J. Am. Chem. Soc. 2013, 135, 519 Liing Wipf Group Page 4 of 14 10/2/2013
5 Higuchi s model study Chem. Eur. J. 2013, 19, 4255 Liing Wipf Group Page 5 of 14 10/2/2013
6 Higuchi s model study Intramolecular oxidabve coupling: Entry Oxidant T[ o C] T Yield [%] 1 Fe(acac) 3 RT [a] 1 h 0 2 Cu(2- ethylhexanoate) 2 RT [a] 2 h 7 3 I min 59 4 ICl h 28 5 NIS h 63 6 PhI(OAc) h 32 [a] AddiBon of oxidant at - 78 o C. Chem. Eur. J. 2013, 19, 4255 Liing Wipf Group Page 6 of 14 10/2/2013
7 An example of a tandem radical cyclizabon/keck allylabon Mechanism: Tetrahedron Le , 38, 8165 Pure Appl. Chem. 2007, 79, 223 Liing Wipf Group Page 7 of 14 10/2/2013
8 Radical- based H- atom transfer/cyclizabon approaches towards oxindoles J. Chem. Soc., Chem. Commun. 1995, 977 Angew. Chem., Int. Ed. 2004, 43, 95 Liing Wipf Group Page 8 of 14 10/2/2013
9 Title paper: retrosynthebc analysis Challenges for C- H arylabon: 1. Nonenolizable and potenbally labile imine substrate 2. PosiBonal selecbvity between two different terbary centers required if imine stereochemistry is not product- determinining J. Am. Chem. Soc. 2013, 135, Liing Wipf Group Page 9 of 14 10/2/2013
10 StarBng material Tetrahedron 1995, 51, 8121 Synthesis 1994, 31 Liing Wipf Group Page 10 of 14 10/2/2013
11 PreparaBon of the core of scholarisine A toluene, 100 C, 33 h, 83% (13:14:unk = 3.0:1.0:0.1) unknown allyltributylstannane, Et 3 B, benzene, air, 75 C, 5 h, 59% 1. TFA, CHCl 3, 0 C, 12 h, 83% 2. Ph 3 P, imidazole, Br 2 ; CH 2 Cl 2, 0 C, 40 min, 86% TMG, TEMPO, air, THF, 50 C, 12 h, 68% 1. NaBH 3 CN, TFA, CH 2 Cl 2, 0 C, 40 min 2. EtOAc, 80 C, 2 h, 91% over two steps 3. IBX, EtOAc, 80 C, 12 h, >85% J. Am. Chem. Soc. 2013, 135, Liing Wipf Group Page 11 of 14 10/2/2013
12 CompleBon of the total synthesis of (+)- scholarisine A 2- iodoaniline, PPTS, PhMe, THF, 4 Å ms, 90 C, 18 h n- Bu 3 SnH, ACHN, toluene, 110 C, :1 4.5 h, 22 18% ; 23 6% (3 steps) [1,5- H atom transfer] [O} [5- exo- trig cyclizaron] + 1.ozonolysis 2.dithiolane formabon 3.Raney Ni desulfurizabon reducbon NIS, CH 2 Cl 2, 23 C, 20 h, 72% or IDSI, CH 2 Cl 2, 20 C, 45 min, 27% J. Am. Chem. Soc. 2013, 135, Liing Wipf Group Page 12 of 14 10/2/2013
13 CompleBon of the total synthesis of (+)- scholarisine A 1. O 3, CH 2 Cl 2, MeOH, 78 C, 2 min; Me 2 S (22 equiv), C 2. NaBH 4 (2.6 equiv), EtOH, CH 2 Cl 2, C, 1.5 h, 68% Lawesson s Reagent, THF, toluene, 110 C, 16 h, 47% Raney Ni, THF, 23 C, 1 h, 86% PhIO, CH 2 Cl 2, 23 C, 98% J. Am. Chem. Soc. 2013, 135, Liing Wipf Group Page 13 of 14 10/2/2013
14 Conclusion An enanboselecbve synthesis of (+)- scholarisine A was completed in 14 steps from known compound (15 steps from commercial materials). Key steps include: an efficient and diastereoselecbve pyrone Diels Alder reacbon to rapidly form the appropriately funcbonalized [2.2.2]- bicycle a radical cyclizabon/keck allylabon to concurrently forge the [3.3.1]- bicycle and C- 20 quaternary center an indolenine annulabon at a nonenolizable terbary center via a novel late- stage radical C H arylabon the use of a pendant hydroxyl group to facilitate the chemoselecbve reducbon of an extremely unreacbve lactam Future work: applying the developed strategy to related targets exploring the scope of the C H arylabon step probing the biochemical potenbal of scholarisine A itself J. Am. Chem. Soc. 2013, 135, Liing Wipf Group Page 14 of 14 10/2/2013
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