Total Synthesis of (-)-Mersicarpine
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1 Total Synthesis of (-)-Mersicarpine Rie akajima, Tsuyoshi gino, Satoshi Yokoshima, and Tohru Fukuyama. J. Am. Chem. Soc. ASAP Published online Eric E. Buck Current Literature January 23, 2010 Eric Wipf Group Page 1 of 17 1/27/2010
2 Isolation and Background (-)-Mersicarpine was isolated from the bark of K. fruiticosa and K. arborea in Kopsia genus comprises over 23 shrubs and trees in tropical Asia with the highest concentration found in Malaysia ver 50 different alkaloids have been isolated from K. arborea. A select few of the isolated alkaloids, most notably, valparicine, have demonstrated cytotoxic properties against drug-resistant KB cells (IC µm). valparicine Lim, K.; iraku,.; Kanki, K.; Koyano, T.; ayashi, M.; Kam, T. J. at. Prod. 2007, 70, Kam, T.; Subramaniam, G.; Lim, K.; Choo, Y. Tetrahedron Lett. 2004, 45, Eric Wipf Group Page 2 of 17 1/27/2010
3 Proposed Biosynthesis leuconolam leuconoxine derivative Water adds from the less hindered face. + + / 2 - Ac (-)-mersicarpine Br Br Br chartellamide A Br Kam, T.; Subramaniam, G.; Lim, K.; Choo, Y. Tetrahedron Lett. 2004, 45, Eric Wipf Group Page 3 of 17 1/27/2010
4 Postulated biosynthesis of other isolated alkaloids by the Kerr group (-)-mersicarpine C 2 Me secoleuconoxine leuconoxine derivative Different theories on the location of (-)-mersicarpine along the biosynthetic route Magolan, J.; Carson, C. A.; Kerr, M. A. rg Lett. 2008, 10, leuconoxine rhazinilam Eric Wipf Group Page 4 of 17 1/27/2010
5 The Kerr groupʼs synthesis of (±)-mersicarpine Cl K 2 C 3, TF then dimethylmalonate C 2 Me C 2 Me Mn(Ac) 3 Ac reflux 67% C 2 Me C 2 Me decomposition 99% reduction/ hydrolysis Very labile indole-amide functionality. C C 2 Me C a, TF 52% LiCl, DMF microwave 150 o C 10 min 65% C 2 Me Magolan, J.; Carson, C. A.; Kerr, M. A. rg Lett. 2008, 10, Eric Wipf Group Page 5 of 17 1/27/2010
6 The Kerr groupʼs synthesis of (±)-mersicarpine C 2 Me Mn(Ac) 3 Ac reflux decomposition DDQ, toluene reflux (70%) C 2 Me Mn(Ac) 3 Me reflux 10% C 2 Me Mn(Ac) 3 Ac reflux 55% C 2 Me Magolan, J.; Carson, C. A.; Kerr, M. A. rg Lett. 2008, 10, % Eric Wipf Group Page 6 of 17 1/27/2010
7 The Kerr groupʼs synthesis of (±)-mersicarpine Cl 1) K 2 C 3, TF (97%) 2) DDQ, toluene reflux (81%) 1) K 2 C 3, TF, reflux (98%) 2) Mn(Ac) 3, Ac, reflux (60%) C ab 4 C C t-buk ac 3, Me (95%) TF (quant) TF (74%) Magolan, J.; Carson, C. A.; Kerr, M. A. rg Lett. 2008, 10, Eric Wipf Group Page 7 of 17 1/27/2010
8 The Kerr groupʼs synthesis of (±)-mersicarpine C C 1) a, CS 2, MeI TF, (73%) 2) DME, microwave, 170 o C (74%, 2 cycles) 1) 2, Pt 2, CCl 3, Boc oxone, acetone, TBAS, EDTA, C 3 C, 2 (93%) Boc 2) Boc 2, 3, DCM (82%, 2 steps) 14 steps, 11% overall yield 1) TBSTf, 2, 6-lutidine, C 2 Cl 2 2) TBAF, TF (82%, 2 steps) (±)-mersicarpine Identical 13 C spectrum and RMS to reported values 1 MR did not match. Chemical shift dependent on acid concentration in CDCl 3 Magolan, J.; Carson, C. A.; Kerr, M. A. rg Lett. 2008, 10, Eric Wipf Group Page 8 of 17 1/27/2010
9 The Zard groupʼs formal synthesis of (±)-mersicarpine C 2 1) (CCl) 2 2) Kt-Bu, t-bu 77% over 2 steps C 2 tbu The t-butyl ester serves to stabilize the radical intermediate and can be easily removed at a later stage. Cl Cl 1) a, Bu 4 S 4, DCM 2)KSC(S), acetone 55% C 2 tbu S S Biechy, A.; Zard, S. Z. rg Lett. 2009, 11, Eric Wipf Group Page 9 of 17 1/27/2010
10 The Zard groupʼs formal synthesis of (±)-mersicarpine C 2 tbu S Ac lauroyl peroxide C 2 tbu Ac C 3 74% S Mn 2 DLP Ac DLP - + C 2 tbu Ac C 3 C 2 tbu Ac Biechy, A.; Zard, S. Z. rg Lett. 2009, 11, C 2 tbu Ac C 3 5:2.5 ratio of desired: quenched product After disappearance of SM Mn 2 was added. Eric Wipf Group Page 10 of 17 1/27/2010
11 The Zard groupʼs formal synthesis of (±)-mersicarpine SCl 2, pyr. 80% Cl Cl Cl Mg (2 equiv) C 2 74% 1) (CCl) 2, DMF 2) 4 2 1) LiAl 4 2) Boc 2, 3 Boc 70% 66% over 2 steps For preperation of 4-ethyl-4-pentenoic acid see: McCaffery, E. L.; Shalaby, S. w. J. rganomet. Chem. 1967, 8, For preperation of 4-ethyl-4-pentenamide see: Biechy, A.; Zard, S. Z. rg Lett. 2009, 11, Biechy, A.; Zard, S. Z. rg Lett. 2009, 11, Eric Wipf Group Page 11 of 17 1/27/2010
12 The Zard groupʼs formal synthesis of (±)-mersicarpine C 2 tbu S S 1) A (3 equiv), DLP (1.4 equiv) 1,2-DCE 2) Mn 2 78% over 2 steps C 2 tbu Boc 1) TFA, toluene 2) 3, Boc 2 84% over 2 steps Boc Boc A Kerr's advaced intermediate 3 steps (±)-mersicarpine 10 steps to Kerr s advanced intermediate in 18% yield (1 fewer step). Biechy, A.; Zard, S. Z. rg Lett. 2009, 11, Eric Wipf Group Page 12 of 17 1/27/2010
13 Title Paper: Eschenmoser-Tanabe fragmentation and indole formation C 2 Me 1) IBX, DMS, 72% C 2 Me 2 C 2 Cl 2) 2 2, a, 2 -Me, 88% aac, 2-89% 25% over 4 steps from cyclohexanone 87% ee to 99% ee 2 IA 2 C 2 Me Pb(Ac) 4 DCM, -10 o C 60% C 2 Me 1) ab 4, 87% 2) A, Pd(PPh 3 ) 4, CuI DMF, 3, 78% 2 C 2 Me aaucl % C 2 Me akajima, R.; gino, T.; Yokoshima, S.; Fukuyama, T. J. Am. Chem. Soc. ASAP Eric Wipf Group Page 13 of 17 1/27/2010
14 Title Paper: Unexpected oxidation C 2 Me Ph 2 Cl, aac i-pr, 2, 1,4-dioxane 97% Ph C 2 Me a, MS4A, toluene; MsCl, 3, 0 o C 77% Ph Ms 2, Pd/C i-pr, C 2 Cl 2 ; Si 2 Unexpected formation of (-)- mersicarpine after prep-tlc purification. Yield were low and irreversible however. (-)-mersicarpine akajima, R.; gino, T.; Yokoshima, S.; Fukuyama, T. J. Am. Chem. Soc. ASAP Eric Wipf Group Page 14 of 17 1/27/2010
15 Title Paper: Control of autoxidation Ph 2 2, Pd/C Ms i-pr, C 2 Cl 2 Ms Ms + (-)-mersicarpine ac 3 i-pr, DCM autoxidation; degassed reaction mixture Me 2 S 96% yield over 3 steps (-)-mersicarpine 16 steps, % akajima, R.; gino, T.; Yokoshima, S.; Fukuyama, T. J. Am. Chem. Soc. ASAP Eric Wipf Group Page 15 of 17 1/27/2010
16 Title Paper: Proposed mechanism of final oxidation 1 autooxidation; Me 2 S (-)-mersicarpine 96% yield over 3 steps The addition of 18 2 gave full incorporation of 18 in the product initiator Me 2 S akajima, R.; gino, T.; Yokoshima, S.; Fukuyama, T. J. Am. Chem. Soc. ASAP Eric Wipf Group Page 16 of 17 1/27/2010
17 Summary 2 distinct approaches to assemble the core The Kerr group constructed (±)-mersicarpine in 14 steps and 11% yield utilizing an oxidation/ radical cyclization sequence to construct the 6 membered ring followed by an imine cyclization to install the 7-memebered ring. The Zard group constructed an advanced intermediated of the Kerr groupʼs (±)-mersicarpine synthesis in 10 steps and 18% yield utilizing an a radical annulation sequence to construct the 6 membered ring. The Fukuyama group completed the total synthesis of (-)-mersicarpine in 10 steps and 3.2 % yield from known cyclohexane. They utilized a Sonogashira coupling and gold catalyzed annulation to install the indole moiety followed by acylation sets the 6 membered ring. Eric Wipf Group Page 17 of 17 1/27/2010
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