VINBLASTINE. H MeO 2 C MeO. OAc. CO 2 Me. Me H
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1 VIBLATIE 2 C 1 C 2 Ac
2 a 3: catharanthine C 2 Ac C 2 2: ( )-vindoline xidation 5' 2 C 3' 16' 20' Ac C 2 1: (+)-vinblastine b 4 C 2 TFAA, -50 C Polonovski fragmentation 6' 5' 16' C 2 5 TFA 4' 3' 15' 16' 21' 20' C 2 6a 2 then ab 4 0 C 16' 2 C Ac C 2 7: anhydrovinblastine 3' C 2 6b 20' 15' cheme 1. General biosynthetic pathway (a) for binary indole-indoline alkaloids such as vinblastine (1) and Potier's synthetic approach (b) based on that hypothesis.
3 C
4 C 2 8 t-bu C 2 9a C 2 9b 2 C 16' 11 C 2 Ac 2 C 2 10 cheme 2. The challenges of establishing the C-16' stereocenter of vinblastine: the "chloroindoline" approach.
5 2 C ing closure s Ts 2 C 16' 20' CF 3 Ac C 2 1: (+)-vinblastine 12 C 2 Ac 2 C 14 s Ts Epoxide opening CF 3 Ac C 2 2: ( )-vindoline Indole chlorination s = 2-nitrobenzenesulfonamide 2 2 C 13 tereocontrolled coupling s 20' Ts CF 3 s 2 C 15 TBDP Fukuyama indole synthesis 2 C TBDP 16 TP 2 C 17 TE TM TBDP 18 TP 18 C Baeyer Villiger oxidation TBDP TBDP Transesterification 2 C 19 TE TM TBDP cheme 3. etrosynthetic analysis of (+)-vinblastine (1): initial stages.
6 22 BaC 3, C 2 2 / Y ' 1. Protection 2. 'MgX or 'Li C ab 4 C 2 2 / C n-bu 3 n, Et 3 B (cat.), toluene, 25 C Y ' n(n-bu) 3 5-exo cyclization ' Y n(n-bu) 3 -[n(n-bu) 3 ] ' Y [n(n-bu) 3 ] Y 31 ' Y ' cheme 4. Fukuyama's synthesis of indoles (32) from quinolines (22). ' Y
7 A C Ac C 2 2: ( )-vindoline C 2 Ms Allylic oxidation Elimination Diels-Alder cycloaddition 34 C 2 Ms Enamine formation Ms C Ds = 2,4-dinitrobenzenesulfonamide 14 C 2 Mitsunobu reaction Ds Ms 37 C 2 Ms C 2 38 Ms 42 Ms TP 41 ucleophilic addition C 2 C 2 Fukuyama indole synthesis Ms 40 C 2 + Ds 39 cheme 5. etrosynthetic analysis of (+)-vinblastine (1): final stages.
8 BF 3 Et 2, toluene, 100 C, 2 h - 43 etro Diels-Alder reaction 44 Intramolecular aza (61%) Diels-Alder reaction (1.5:1 ds) Li C(Et) 2 C(Et) p-ts, acetone/ 2, 25 C, 2 h; C, Et 3, 80 C C 47 Intramolecular Diels-Alder reaction (50%) C 48 C 2 49: pseudotabersonine cheme 6. Grieco's total synthesis of the alkaloid pseudotabersonine (49) based on a Diels-Alder design. (1993) 17
9 a 50: glycerol, 2 51: acrolein [] 54 -[ 2 ] 53 b 3 /TF (1:1), 80 C K, DM 56 Ts (5:1 to 14:1 regioselection) 57 Ts 80 to 140 C 58 cheme 7. The classical kraup quinoline synthesis (a) and Fukuyama's modified approach (b) using -aryl--sulfonylaminopropionaldehydes (56).
10 Ms, a 2 C 3, TF/ 2, TP 0 C; ab 4, 2. C 2, 0 C Ms Ms C a (80%) C TF, 0 C 43 DP = 1. DP, CA, C 2 2, 25 C n-bu 3 n, AIB, toluene, 110 C (66% overall from 59) C 2 C 2 Fukuyama indole synthesis Ms 40 C , Et 3, 4-DMAP, C 2 2, 25 C 2. 2, Pd/C, Et, 25 C; 2, C, aac, Ac/Et, 25 C 3. CA,, 25 C (71% overall) Ms 60 TP C 2 C 2 cheme 8. ynthesis of indole building block 40.
11 61 PhMgBr, TF Ph Ds = 2,4-dinitrobenzenesulfonamide g(ac) 2 (cat.), aac (cat.),, 8 h aisen rearrangement Ph (79% overall from 61) C 66 (91%) 3,, C 2 2, -78 C; then 2 C Ph 1. ac, Ac 2. Ac 2, py 3. Lipase P, TF/ 2, 50 C (42% overall) (97% ee) Ph C 67 Ms, Et 3, toluene, 0 80 C (71%) C 68 LiAl 4, TF, C; 2, a; Ds, C 2 2 (75%) Ds 39 cheme 9. ynthesis of amine building block 39.
12 Ds Ms 40 C 2 DEAD, Ph 3 P, C 6 6, 25 C, 30 min Ds 39 (79%) DEAD = diethyl azodicarboxylate Ms 38 TFA, 2, C 2 2, 25 C, 1 h C 2 pyrrolidine, /C 3 C (5:1), Ms 36 C C, 3 h Ms 37 C 2 -[ 2 ] Enamine formation Ms 35 C 2 Diels-Alder reaction (73% overall from 38) Ms 34 C 2 cheme 10. ynthesis of advanced intermediate 34.
13 Ms A 34 E C 2 1. Ph 3 P, C 4, C, 70 C, 30 min; 4 2. K,, 80 C, 45 min 69 C 2 t-buk, I, TF, 0 C, 90 min (81% overall from 34) (Phe) 2, C 6 6, C 2 80 C, 30 min (88%) 70 C 17 C 2 mcpba, /C 2 2 (1:9), sat. aq. ac 3, 0 C, 5 min C C (37% aq.), ab 3 C, / (1:9), 0 C, 5 min; ab 3 C, 25 C, 30 min, a 2 C 3 C 2 (64% overall from 33) C 2 2: ( )-vindoline Ac cheme 11. Completion of ( )-vindoline (2). Ac 2, aac, 25 C, 4 h (91%) 73 C 2
14 Piv, Et 3, (i-pr)ti 3, Et 2, 0 C; i-pr 2 Et, Li C, C 2 2, 0 C (73% from 74) C TBDP DIBAL-, C 2 2, -78 C 2, aac, Et, 25 C aq. a, C 2 2, 25 C C 78 TBDP TBDP TBDP TBDP ab 4, TF/ 2 2. TBDP, imid, DMF (85% overall) itrile oxide 1,3-dipolar cycloaddition (59% overall from 78) C 77 Zn, Ac, 25 C, 4 h (66%) 2 C TE TM 19 TBDP 1., K 2 C 3 2. TE; TM (74% overall from 20) TBDP 20 mcpba, Ac, 25 C Baeyer-Villiger oxidation TBDP 21 cheme 12. ynthesis of building block 19.
15 2 C TE TM TBDP 19 TP TE TM LDA, Li TF, C C C 2 C TBDP (76%) 83 TP 2 C n-bu 3 n, Et 3 B, TF, 25 C (67%) 16' 17 TE TM Fukuyama indole synthesis TBDP 2 C (84%) 6' 85 3' TBDP p-ts, n-bu 2 n, Et 3, C 2 2, 25 C 1. 2, Et 3, 4-DMAP, C 2 2, 25 C 2. Ac/ 2 (19:1), 80 C (62% overall) TP 2 C 84 TE TM TBDP 2 C 86 Ts TBDP 1. ac 3, DMF, 80 C 2. s 2, DEAD, Ph 3 P, toluene, 25 C (79% overall) s 2 C 87 TBDP K 2 C 3, DMF, 80 C (82%) s CF 3 1. TFA, C 2 2, 25 C 2. p-ts, C 3 C/toluene, 2 (C 2 ) TFAA, py, C 2 2, 25 C 2 C (67% overall) 2 C Ts cheme 13. ynthesis of advanced intermediate 14. s TBDP
16 2 C 14 s Ts CF 3 t-bu, C 2 2, 0 C 2 C s Ts 89 CF 3 Isomerization 2 C (97% overall from 14) 13 s Ts 2 CF 3 C 2 2 Ac, TFA, C 2 2, 0 25 C 2 C s Ts 90 CF 3 Ts 2 C s 16' CF 3 20' 1. Et 3, 2. C 2 C 2, DBU, C 3 C 3. ac 3, i-pr/ 2 C 2, Ac (1:1), 25 C Ac (50% overall) C 2 C : (+)-vinblastine cheme 14. Final stages and completion of the total synthesis of (+)-vinblastine (1).
17 ' '
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