Total Synthesis of the Chartellines
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1 Total Synthesis of the Chartellines X Y chartelline A, X = Y = chartelline B, X =, Y = chartelline C, X = Y = Mariam Shamszad ovember 1, 2006
2 Background Chartellines A, B, and C were isolated in the 1980s by Christophersen and co-workers Isolated from the marine bryozoan Chartella papyracea collected in the orth Sea Chartelline A lacks completely lacks any significant biological activity but remains a target of interest due to its novel and complex structure In 2006, the Weinreb group reported their progress toward the total synthesis of chartelline A and the Baran group reported the first total synthesis of chartelline C
3 The Chartellines as Synthetic Targets Structure and stereochemistry of chartelline A confirmed by X- ray crystallography 10-membered ring adopts a rigid tube-like conformation, indicating little conjugation present between the ring systems Indolenine system almost perpendicular to the spiro-β-lactam ring and is close to parallel to the imidazole ring Dense array of sensitive functionalities: spiro-β-lactam, indolenine, chloroenamide, and 2-bromoimidazole units
4 Weinreb s Retrosynthesis of Chartelline A chartelline A C P' P' P + Li P' Sun, C.; Lin, X.; Weinreb, S. M. J. rg. Chem. 2006, 71, 3159.
5 Model Studies 1) p- anis idine E t, Ac 2) C 2 C E t 3, C % PM P (TM S) 3 S i A IB P h 100 o C 91% P MP 1) Cbz a, TF 2) CA, C 83% Cbz P h p- Ts Ph 100 o C 67% C Cbz P h 2 p-anisidine
6 More Model Studies P MP 1) () 2 DM AP, Et 3 C 2 2, 91% 2) TF Li -78 o C, 96% t -Bu P MP TFA, 0 o C C 2 2, 91% or n-b u 4 Re 4 p-ts C 2 2, rt 100% X X = X = P MP LiB 4, TF 0 o C, 56% PM P TFA C % PM P undes ired
7 Synthesis of Tribrominated β-lactam Moiety 2 1) p- anis idine P h,! 2) C 2 C E t 3, P h 74% 2 PM P (B oc ) 2 DM AP Et 3 C % 2 B oc P MP 1) Zn, A c TF 2) (TM S) 3 Si AIB, Ph 88% 2 PM P B n 3 3 CaC 3 2 C % PM P t -Bu Cu 2 C 88% P MP B oc CA, 2 C, 90%
8 Preparation of Imidazole Fragment C 2 E t T r, Et 3 C 2 2, rt 96% T r C 2 Et tb uk, I 18-C-6, TF -78 o C 95% Tr C 2 E t 1) LiA l 4 TF, 99% 2) A c 2, pyr DMA P C 2 2, 97% T r Ac B M C,! 86% B M Ac More Efficient Route: BM C 2 Et BM Et 3 TF, 0 o C 55% C 2 Et 1) tbuk, I 18-C-6, TF BM -78 o C, 84% 2) BM (cat) TF,! 86% C 2 Et + BM C 2 Et C 2 Et
9 Completion of Imidazole Fragment B M C 2 Et Bn 3 3 CaC 3 C % BM C 2 Et S nb u 3 CsF, Pd 2 (dba) 3, t-b u 3 P diox ane, 100 o C 80% B M C 2 Et 1) s4, M 2, 2 C 2) 2 C, 2 S 4 73% B M C 2 E t B S, TF 95% B M C 2 Et DIB AL C o C 98% B M B M K 2 C 3, 0 o C to rt P() %
10 Coupling of Fragments B oc + B M 2 eq. LiMDS TF, - 78 o C 91% B oc B M 2 equiv 1) TFA. TF 2, rt, 99% 2) Pb(A c) 4 Ph, r t B oc C B M p-ts Ph rt B oc C B M B oc BM B oc BM undes ired desired
11 ew thodology BM + I C 2 B M 10 m ol% CuI Cs 2 C 3, TF 70 o C BM B M C 2 45% ( 67% br sm ) Sun, C.; Camp, J. E.; Weinreb, S.M. rg. Lett. 2006, 8, 1779.
12 Baran s Approach to Chartelline Carboskeleton C 2 C 2 R R chartelline C there are no examples for such a ring contraction of a pyrroloindoline unit and ample precedent that suggests its failure X R' R" R not observed X =,,, Se, etc. R' R R" Baran, P.S.; Shenvi, R. A.; Mitsos, C. A. Angew. Chem., Int. Ed. 2005, 44, 3714.
13 Synthesis of Chartelline Carboskeleton TBS 2 C 2 M g TF, -78 o C 93% TB S 2 1) KCS, 4 toluene, 110 o C 2) 3) i. 2 2, TF ii. a/sat. ac 3 4) TBS, Et 3 C % TBS 1) ai 4, s 4 TF/ 2 2) K 2 C 3, C P( )(E T) % 2 C TB S B oc Pd(PP h 3 ) 4 CuI, 71% 2 C TBS 1) Pd/C, 2 Et 2) TB AF, TF 3) Mn 2, C % C 2 C
14 Continued P()(Et) 2 1) Li, TF/ 2 2) BP, DIPEA 0 o C 2 P()(Et) 2 C 2 86% C C 2 DIPEA, Li C 3 C, 70 o C 75% C 2 1) 180 o C 2) BS, KC 3 TF/ 2 C 2 [1,2] 88% C 2 19% overall yield 10 steps
15 Dead End Routes to the Chartelline Skeleton C 2 2 R Ring-closing metathesis Macrolactamization C 2 eck-type ring closure
16 Baran s Total Synthesis of Chartelline C 2 C I + TB S Pd(PP h 3 ) 4 CuI DM E:E t 3 85% 2 C B oc TBS 1) Raney i, 2) TB AF, TF 3) Mn 2, C % over 3 steps C 2 C 1) Li, TF/ 2 2) BP, DIP EA 0 o C 2 C P( )(E t) 2 C 2 89% R = TM SE P( )(E t) 2 C 2 R DIP EA, Li C 3 C, 70 o C 56% Baran, P.S.; Shenvi, R. A. J. Am. Chem. Soc. 2006, ASAP.
17 Continued B oc C 2 R 2, BA Ph 36%, 60% bas ed on recovered dibromide interm ediate C 2 R 185 o C, C 3 C BS C 2 R K 2 C 3, 18-C-6 C 2 R br ine w/up C 2 R 93% TFA/DCE (1:1) ; o-dcb, 200 o C 64% [- C 2 ] 64% chartelline C 10 steps from indole from eck coupling
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