Towards Maoecrystal V: A Comparison of Recent Strategies
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1 Towards Maoecrystal V: A Comparison of Recent Strategies Reactant/Reagent Current Literature: November 14, 2009 lissa Sprachman lissa Wipf Group Page 1 of 14 12/28/2009
2 Maoecrystal V: Structural RepresentaGons X-Ray Crystallographic Structure rg. Lett. 2004, 6, lissa Wipf Group Page 2 of 14 12/28/2009
3 IsolaGon and Structural InformaGon Isolated from the leaves of Isodon eriocalyx (Chinese medicinal herb) Structural confirmagon: 1D and 2D NMR, MS, X Ray Inhibitory acgvity toward ela cells (IC 50 = 0.02 μg/ml) [Compare to cis plagn: IC 50 = 0.99 μg/ml) Copied from: rg. Lett. 2004, 6, lissa Wipf Group Page 3 of 14 12/28/2009
4 ent -kaurene The ent Kauranes (diterpenoids) Related Structures: Epi-eriocalyxin A Maoecrystal N Maoecrystal Ac C C 2 C 2 For a review see Nat. Prod. Rep. 2006, 23, 673. Acta Botanica Yunnanica, 1997, 19, 191. Proposed Biogenetic Pathways for Maoecrystal V and Maoecrystal Z from a common 7,20-epoxy-ent-kaurane: Maoecrystal Z Ac C [] C C rg. Lett. 2006, 8, C2 C2 C -C 2 lissa Wipf Group Page 4 of 14 12/28/2009
5 Danishefsky: TL 2009, 50, Summary of Routes + MM MM TBS C 2 IMDA MM C 2 Br Baran (Li): rg. Lett. 2009, 11, 4744 and rg. Lett. 2009, 11, TBS Bi + MM 3 TBS xidative Dearomatization TBS Ac IMDA Ac TBS Nicolaou: Chem. Commun. Advance MM TBS 2 C C2 lissa Wipf Group Page 5 of 14 12/28/2009
6 Danishefsky: PaZern RecogniGon PG TBS PG + 1. Pd(Ac) 2 ligand, K 3 P 4, TF, 80 o C, 12 h 91% 2. TMSCN 2, DIPEA C 3 CN/, 9:1 quant. 1. Bu 3 SnC 2 MM, BuLi, TF, -78 o C to -40 o C 30 min, 0.5% workup, 75% 2. /, 50 o C, 75% 3. Piv, pyr, DCM, 12 h, 96% Piv Br 1. NaB 4, Ce 3, 0 o C, 2 h, 93% 2. MM, DIPEA, DCM, 12 h, 95% MM Piv 1. DIBAL, -78 o C DCM, 30 min, 95% 2. K, 18-crown-6, IC 2 SnBu 3, 0 o C, TF, 6 h, 90% MM SnBu 3 ligand = P(tBu) 2 Pattern Recognition: J. rg. Chem. 2007, 72, lissa Wipf Group Page 6 of 14 12/28/2009
7 Danishefsky (cont.) MM SnBu 3 n-buli MM -78 o C to -20 o C, TF, 6 h, 88% Li, N 3 (l), t-bu TF, -78 o c, 20 min, -33 o C, 40 min MM 1 N MM TF,, 10:1 0 o C, 8 h 78% over 2 steps 1. 2 C MM Pyr, DCM, 0 o C, 72% 2. TBSTf, Et 3 N, DCM, 0 o C, 15 h, 81% TBS C 2 α:β = 1 : 3 Incorrect Facial Selectivity from IMDA: o C sealed tube toluene, 12 h MM C 2 2. TBAF, 0 o C, TF 48% (2 steps) lissa Wipf Group Page 7 of 14 12/28/2009
8 Nicolaou: Core Structures for EvaluaGon C 2 Pd(TFA) 2 Ag 2 C 3 DMF/DMS (20:1) 80 o C, 3 h, 89% 1. BBr 3 C 2 2, -78 o C to 0 o C 2 h, 98% 2. MM, TF, 0 o C, 2 h, 56% MM 1. Na, TF, then Br 2 C N TF, 0 to 23 o C, 8 h 2. Na 2 C 3, I,, reflux, 2 h, 57% 2 C MM 1. TBSTf, Et 3 N C 2 2, 0 o C, 2 h 2 C MM TBS 2. K 2 C 3 hydroquinone then 1 N (50%, 2 steps) 3. 6 N (aq), reflux, 3 h (83%) C2 lissa Wipf Group Page 8 of 14 12/28/2009
9 Nicolaou (cont.) C2 PIFA KC 3, 0 to 23 o C, 0.5 h, 83% C2 2, Pd/C C2 + PIFA C 2 I, KtBu 18-crown-6 42% (3 steps) C2 Na C2 lissa Wipf Group Page 9 of 14 12/28/2009
10 Nicolaou: Simplified structure/interesgng approach to the TF C2 exo:endo: > 20: N Na(aq) Et, 60 o C 5 h 2. (C) 2, DMF, C 2 2 reflux, 1 h 3. TMSCN 2, TF/C 3 CN, 1:1 0 o C, 2 h, 79% (3 steps) N 2 Rh 2 (Ac) 2 (10 mol%) C 2 2, 23 o C 1 h Silica gel 75% 2, Pd/C EtAc, 23 o C, 24 h (87%) Tested three "core" structures against cell lines: A B C nly C showed moderate (but nonselective) activity against human tumor cell lines. lissa Wipf Group Page 10 of 14 12/28/2009
11 Baran: xidagve DeramoGzaGon and IMDA TBS Bi MM 3 DBU, toluene 67% (dr = 7:3 TBS MM Li(t-Bu)3 Al TF, -78 o C 72% TBS MM DIPEA DMAP DCM -78 o C 69% TBS MM TFA, DCM, 0 o C 65% TBS Pb(Ac) 4 Ac, 81% (dr = 7:3) TBS Ac (Major) 165 o C, o-dcb BT 79% TBS Ac Ac TBS 1. 2, Pd/C 97% 2. SmI 2 78% (dr = 17:3) TBS lissa Wipf Group Page 11 of 14 12/28/2009
12 ReacGons of Note Arylation with a Bi(V) species: TBS Bi MM DBU, toluene 3 TBS Ar Ar Bi Ar Ar 2 Bi TBS Applications of Bi(V) species include phenol oxidation alpha-arylation: MM Tetrahedron 2006, 62, Wessely oxidation/diels Alder: Et C 2 Et Ac Pb(Ac)4, Ac C 2 Et 140 o C 72% 89% Et Et 2 C Et Ac Et (+/-)-coronafacic acid J. Chem. Soc., Chem. Commun. 1990, 739. lissa Wipf Group Page 12 of 14 12/28/2009
13 Li (Same Approach?) B() 2 MM Pb(Ac) 4 g(ac) 2 C 3, 60 o C Pb(Ac) 3 MM C 2 Pyr, C 3 then + 70% 1. TMS, imid. C 2 2, 0 o C 2. DIBAL-, C o C to rt, then 85% (2 steps) EDCI, DMAP Ac Ac 70% Pb(Ac) 4 Ac 92% (mixture of diastereomers; separated at this stage toluene, 130 o C 82% 2, Pd/C 90% Ac SmI 2, TF t-bu, rt 68% + 2 : 1 (w/ free alcohol as substrate: 3.8 : 1 lissa Wipf Group Page 13 of 14 12/28/2009
14 Summary and utlook Several groups have reported approaches to Maoecrystal V, all involving a dearomagzagon and IMDA reacgons. nly Nicolaou and coworkers have successfully installed the key TF moeity. Although Baran and coworkers pose an enangoselecgve approach, the need for improved diastereoselecgviges is apparent. Even the advanced Maoecrystal V intermediate (Nicolaou) did not exhibit comparable biological acgvity to that of the natural compound; is a viable total synthesis necessary for making a useful therapeugc? lissa Wipf Group Page 14 of 14 12/28/2009
Total Synthesis towards Maoecrystal V
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