Total Synthesis of Rubriflordilactone A
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1 Total Synthesis of Rubriflordilactone A Jian Li, Peng Yang, Ming Yao, Jun Deng, and Ang Li. J. Am. Chem. Soc., 2014, 136 (47), pp Liming Cao Wipf Group Current Literature 1/3/2015 Liming Wipf Group Page 1 of 11 1/3/2015
2 Schisandraceae triterpenoids Schisandraceae is a family of climbing plants and contains the genera Schisandra and Kadsura. The family consists of 50 species mainly distributed in southeast Asia and North America. Many species have a long history of use as folk medicines in China and are hot topic since 1970 s because of their remarkable medicinal funcwons. Schisandraceae triterpenoids embody complex and dense polycyclic frameworks and are embellished with diverse oxy- funcwonaliwes and intricate stereochemical pa[erns. Only example: (±)- Schindilactone A (29 steps, 0.2%) Nat. Prod. Rep. 2008, 25, 871 Phytochem. Rev. 2014, DOI: /s Angew. Chem., Int. Ed. 2011, 50, 7373 (±)- Schindilactone A Liming Wipf Group Page 2 of 11 1/3/2015
3 Rubriflordilactone A and B Schisandra rubriflora is a deciduous Climber in the forests and shrubberies to 3300 meters in the Himalayas and is widely used in the tradiwonal Chinese medicine. Rubriflordilactone A and B were isolated from the leaves and stems of Schisandra rubriflora by Sun et al. in 2006 and characterized by 2D NMR and X- ray crystallography. Rubriflordilactone A and B possess a mulwsubswtuted arene mowf in their pentacyclic frame work. Rubriflordilactone B exhibited promising anw- HIV acwvity. Org. LeG. 2006, 8, 991 h[p:// Liming Wipf Group Page 3 of 11 1/3/2015
4 Yang s Synthesis of the Racemic 5,7- Bicyclic System Et 2 AlCl (1.4 equiv), toluene, 0 C, 30 min 65 % b) MeMgBr (1.6 equiv), THF, 78 C to 0 C, 1 h 78 % c) KHMDS (1.5 equiv), THF, 78 C to 0 C; P(OMe) 3 (1.5 equiv), O 2, 0 C, 1 h, 75 % d) TESOTf (1.5 equiv), 2,6- luwdine (1.5 equiv), CH 2 Cl 2, 0 C, 30 min, 95 % e) KOtBu (3.0 equiv), CHBr 3 (3.0 equiv), petroleum ether 20 C, 30 min. f) AgClO 4 H 2 O (2.0 equiv), acetone, 30 C, 10 h 82 % for 2 steps steps 5,7- Bicyclic System (±)- Schindilactone A Angew. Chem., Int. Ed. 2011, 50, 7373 Liming Wipf Group Page 4 of 11 1/3/2015
5 RetrosyntheWc Analysis Liming Wipf Group Page 5 of 11 1/3/2015
6 Synthesis of the Right- Hand Segment a) 8 (5 mol %), BH 3 THF (0.67 equiv), THF, 0 C, 30 min, 82%, > 99% ee b) Pd(PPh 3 ) 2 Cl 2 (0.5 mol %), CuI (1 mol %), TMS- acetylene (3.0 equiv), toluene, 50 C, 2 h, 99% c) 2- nitrophenol (2 mol %), EtC(OMe) 3 (1.7 equiv), 100 C, 48 h 90%, 7.5:1 dr at C20 d) aq LiOH (1.0 M)/THF (1:1), 60 C, 4 h, 93% e) NIS (1.0 equiv), NaHCO 3 (2.0 equiv), acetonitrile, 22 C, 1.5 h, 52% Liming Wipf Group Page 6 of 11 1/3/2015
7 Synthesis of the Les- Hand Segment a) Cu(OTf) 2 (5 mol %), 16 (5.5 mol %), 4 Å MS, CH 2 Cl 2, 0 C, 2 d, 80%, 76% ee b) EtSH (3.0 equiv), BuLi (2.5 equiv), THF, 0 C, 30 min, 96% c) Pd 2 (dba) 3 (1 mmol %), S- Phos (5 mmol %), MeZnI (5.0 equiv), NMP/THF (1.5:1), 65 C, 1.5 h, 80% d) MeMgCl (1.1 equiv), THF, 40 C, 1 h, then 20 C, 45 min, 83% e) KHMDS (1.1 equiv), THF, 78 C, 30 min; then P(OMe) 3 (1.5 equiv), O 2, 78 C, 20 min, 83% f) TESOTf (1.5 equiv), 2,6- luwdine (1.5 equiv), CH 2 Cl 2, 0 C, 30 min, 94% g) CHBr 3 (3.0 equiv), t- BuOK (3.0 equiv), petroleum ether, 20 C, 1 h h) AgClO 4 H 2 O (2.0 equiv), CaCO 3 (5.0 equiv), acetone, 30 C, 10 h, 66% (2 steps) recrystallized to give the enanwoenriched form (73%, > 99% ee) aser removal of the essenwally racemic crystals Liming Wipf Group Page 7 of 11 1/3/2015
8 Synthesis of the Les- Hand Segment i) Pd/C (4 mol %), H 2 (1 atm), MeOH/EtOAc (1:1), 22 C, 1.5 h, 97% j) LiHMDS (2.5 equiv), PhNTf 2 (1.8 equiv), THF, 25 C, 2 h, 89% k) Sc(OTf) 3 (10 mol %), Ac 2 O (5.0 equiv), acetonitrile, 10 min, 96% l) LiHMDS (1.6 equiv), THF, 0 C, 5 min, 93% m) Et 3 SiH (25.0 equiv), BF 3 OEt 2 (20.0 equiv), 35 C, 3 h, 65% (29% for the recovered SM) n) Pd(PPh 3 ) 4 (10 mol %), Me 3 SnSnMe 3 (1.5 equiv), LiCl (1.5 equiv), THF, 60 C, 15 min, 75% Liming Wipf Group Page 8 of 11 1/3/2015
9 CompleWon of the Synthesis a) Pd(PPh 3 ) 4 (10 mol %), CuTC (1.5 equiv), NMP, 10 min, 96% b) O 2, DMSO, 145 C 45 min, 73% c) LiAlH(Ot- Bu) 3 BF 3 - OEt 2 acetylawon Liming Wipf Group Page 9 of 11 1/3/2015
10 CompleWon of the Synthesis a) Pd(PPh 3 ) 4 (10 mol %), CuTC (1.5 equiv), NMP, 10 min, 96% b) O 2, DMSO, 145 C 45 min, 73% c) LiAlH(Ot- Bu) 3 (1.1 equiv), THF, 5 C, 10 min d) DAST (2.0 equiv), CH 2 Cl 2, 22 C, 10 min, 62% (2 steps) e) BF 3 OEt 2 (3.2 equiv), CH 2 Cl 2, 22 C, 5 min, 66% Liming Wipf Group Page 10 of 11 1/3/2015
11 conclusion The first and asymmetric total synthesis of Rubriflordilactone A in 19 steps (2%). The two segments were prepared in essenwally enanwopure forms and assembled through SWlle Migita coupling; the geometry of the triene was secured. A one- pot 6π- electrocyclizawon/oxidawve aromawzawon served as the key step of the synthesis.. A formal vinylogous Mukaiyama aldol reacwon installed the butenolide side chain at the final stage. Liming Wipf Group Page 11 of 11 1/3/2015
Reporter: Yue Ji. Date: 2016/12/26
Literature Report (11) Total Synthesis of Rubriflordilactone B Reporter: Yue Ji Checker: Mu-Wang Chen Date: 2016/12/26 Yang, P.; Yao, M.; Li, J.; Li, Y.; Li, A.* Angew. Chem. Int. Ed. 2016, 55, 6964. Laboratory
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