Syntheses of Leucascandrolide A. Supergroup Meeting August 4 th, 2004 Yu Yuan
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1 Syntheses of Leucascandrolide A Supergroup Meeting August 4 th, 2004 Yu Yuan
2 Leucascandrolide A Me Me Me Dambrosio, M.; Guerriero, A.; Debitus, C.; Pietra, F. elvetica Chimica Acta 1996, 79, 51-60
3 Me 1 Isolation And Biology Me Isolation: The macrolide is isolated by Pietra and coworkers from the calcareous sponge Leucascandra caveolata along the east coast of ew Caledonia. Biology: The macrolide displays strong cytotoxic activity in vitro on human KB and P388 cancer cell lines (IC 50 = 50 and 250 ng/ml) as well as antifungal activity. rigin: The origin of Leucascandrolide A is not clear. It may be a product of opportunistic microbial colonization of the sponge. Dambrosio, M.; Guerriero, A.; Debitus, C.; Pietra, F. elvetica Chimica Acta 1996, 79, 51-60
4 Me 1 Synthetic Efforts Me Total Synthesis: J. L. Leighton I. Paterson E. M. Carreira S. A. Kozmin Formal Total Synthesis: S. D. Rychnovsky P. Wipf M. T. Crimmins D. R. Williams ornberger, K. R.; amblett, C. L.; Leighton, J. L. J. Am. Chem. Soc. 2000, 122, Paterson, I.; Tudge, M. Angew. Chem. Int. Ed. 2003, 42, 343 Wang, Y.; Janjic, J.; Kozmin, S. A. J. Am. Chem. Soc. 2002, 124, Fettes, A.; Carreira, E. M. Angew. Chem. Int. Ed. 2002, 41, 4098 Kopecky, D. J.; Rychnovsky, S. D. J. Am. Chem. Soc. 2001, 123, 8420 Wipf, P.; Reeves, J. T. Chem. Comm. 2002, 2066 Crimmins, M. T.; Siliphalvanh, P. rg. Lett. 2003, 5, 4641 Williams, D. R.; Patnaik, S.; Plummer, S. V. rg. Lett. 2003, 5, 5035 Dakin, L. A.; Panek, J. S. rg. Lett. 2003, 5,
5 Me 1 Leighton s Synthesis Me xymercuration Brown Crotylation Me Semmelhack Alkoxycarbonylation Allylation Yamaguchi Diastereoselective Zincation ornberger, K. R.; amblett, C. L.; Leighton, J. L. J. Am. Chem. Soc. 2000, 122, 12894
6 Me 1 Leighton s Synthesis Me TBS gclac, acetone, 5 mol% Yb(Tf) 3, 0 C to rt 76% gcl TBS 4 mol% Rh(acac)(C) 2, 4 mol% P(-o-t-BuPh) 3, 0.50 equiv DABC, 800 psi 1:1C/ 2, EtAc, 50 C 62% TBS (E)-crotyl-(-)-diisopino campheylborane, BF. 3 Et 2, TF, -78 C; a, 2 2 TBS 67% 2 mol% Rh(acac)(C) 2, 8 mol% PPh 3, 400 psi 1:1 C/ 2, TF, 50 C 89% TBS ornberger, K. R.; amblett, C. L.; Leighton, J. L. J. Am. Chem. Soc. 2000, 122, 12894
7 Me 1 Leighton s Synthesis Me 1. Ac 2, DMAP, pyridine, C 2 Cl 2 TBS 1. n-bu 4 F, TF, 62% 2. (CCl) 2, DMS, Et 3, C 2 Cl 2, -78 C to -40 C 3. allyl-(-)-diisopino campheylborane, Et 2, -78 C to rt; a, 2 2, 75% TBDPS 2. 2 C=CC 2 SiMe 3, Ti(-i-Pr) 2 Cl 2, C 2 Cl 2, -78 C mol% PdCl 2, 4 equiv CuCl 2, 1 atm C, Me:PhC (1:1) 2. Me 3 BF 4, Proton Sponge, 4 Å MS, C 2 Cl 2,72% TBS 1. TBDPSCl, imidazole, DMF 2. Ac, 2, 40 C, 98% Me TBDPS C 2 Me ornberger, K. R.; amblett, C. L.; Leighton, J. L. J. Am. Chem. Soc. 2000, 122, 12894
8 Me 1 Leighton s Synthesis Me Me TBDPS 3, C 2 Cl 2, -78 C; PPh 3, rt Me TBDPS 1. 4-Methyl-1-pentyne, Cy 2 B, Et 2 Zn,,-dibutylaminoethanol, Ti(-i-Pr)4, toluene, -40 to -20 C, 60% 3:1 ds C 2 Me 93% C 2 Me 2. KSiMe 3, Et 2, TBDPS Me 2 C 1. 2,4,6-trichlorobenzoyl chloride, Et 3, DMAP, Ph, 76% 2. TBAF, TF, 77% Me ornberger, K. R.; amblett, C. L.; Leighton, J. L. J. Am. Chem. Soc. 2000, 122, 12894
9 Me 1 Leighton s Synthesis Me C 2 Me 1. n-buli, C 2, TF, -78 C to 0 C 2. Lindlar's catalyst, quinoline, 1 atm 2, EtAc, 73% 2 C C 2 Me i-buccl, -Me-Morpholine, Ser-Me. Cl, TF 75% C 2 Me C 2 Me DAST, C 2 Cl 2, -20 C; BrCCl 3, DBU, 0 C 64% Me 2 C CBr 4, PPh 3, Br DIBAl-, 2,6-lutidine, TF, 0 C C 3 C 86% 83% n-bu 3 SnC=C 2, Pd 2 dba 3, tri(2-furyl)phosphine, TF, reflux 82% C 2 Me C 2 Me C 2 Me C 2 Me ornberger, K. R.; amblett, C. L.; Leighton, J. L. J. Am. Chem. Soc. 2000, 122, 12894
10 Me 1 Leighton s Synthesis Me 1. 9-BB, TF, (CCl) 2, DMS, Et 3, C 2 Cl 2, -78 C to 0 C. C 2 Me C 2 Me Me (CF 3 C 2 ) 2 P()C 2 C 2, EDCI. Cl, Bt. 2, C 2 Cl 2 Me C 2 CF 3 P C 2CF 3 ornberger, K. R.; amblett, C. L.; Leighton, J. L. J. Am. Chem. Soc. 2000, 122, 12894
11 Me 1 Leighton s Synthesis Me Me C 2 CF 3 P C 2CF 3 + C 2 Me KMDS, 18-crown-6 C 3 C, TF, -100 C 55% Me Me Me ornberger, K. R.; amblett, C. L.; Leighton, J. L. J. Am. Chem. Soc. 2000, 122, 12894
12 Me 1 Rychnovsky s Synthesis Me Conceptualization of the aldol-prins reaction to avoid oligomerization: R + R' LA R LA R ligomers R' u- LA R' Cyclization and work-up u R' Kopecky, D. J.; Rychnovsky, S. D. J. Am. Chem. Soc. 2001, 123, 8420
13 Me 1 Rychnovsky s Synthesis Me Aldol-Prins Myers' Aux Me oyori Yamaguchi Chelation-controlled Stannylation Kopecky, D. J.; Rychnovsky, S. D. J. Am. Chem. Soc. 2001, 123, 8420
14 Me 1 Rychnovsky s Synthesis Me a-d TBS Bn Et Bn I e, f g-i Bn Bn (a) [(R)-BIAP]-RuCl(C 6 6 ), 80 atm 2, Et, 96%, 94% ee; (b)tbscl, imidazole, DMF, 86%; (c) DIBAL, TF, -25 C, 88%; (d) PPh 3,I 2, imidazole, C 2 Cl 2, quant.; (e) combine LDA, (-)-pseudoephedrine propionamide, LiCl, then add the iodide, TF, -78 C, 98%, >20:1 dr; (f) 2 2 S 4, dioxane, 95 C, 77%; (g) i. DIBAL, C 2 Cl 2,-78 C,ii.Ac 2, DMAP, pyridine, 95%; (h) Allyltrimethylsilane, BF 3. Et 2, C 2 Cl 2 ; -78 C, 97%, >20:1 dr; (i) 3, C 2 Cl 2, -78 C, then PPh 3, 95% Kopecky, D. J.; Rychnovsky, S. D. J. Am. Chem. Soc. 2001, 123, 8420
15 Me 1 Rychnovsky s Synthesis Me j-k l, m TIPS TIPS Et TMS TIPS TMS n-p TIPS (j) 2 CC 2 Et, SnCl 2,C 2 Cl 2, 72%; (k) [(S)-BIAP]-RuCl(C 6 6 ), 4 atm 2, Et, 100 C, 51%, >95% ee; (l) TMSCl, Et 3, C 2 Cl 2, 91%; (m) i. CeCl 3,TMSC 2 MgCl, TF/Et 2,-78 Cto23 C,ii.Si 2 gel, C 2 Cl 2, 87% (n) ClC 2 CCl, pyridine, C 2 Cl 2, 95%; (o) i. DIBAL, C 2 Cl 2,-78 C,ii.Ac 2, DMAP, pyridine, 95%; (p) Li, 3,TF, -78 C, 65% Kopecky, D. J.; Rychnovsky, S. D. J. Am. Chem. Soc. 2001, 123, 8420
16 Me 1 Rychnovsky s Synthesis Me TMS Bn + a Bn TIPS TIPS TBS b-f Me (a) i. BF 3. Et 2, 2,6-di-tert-butylpyridine, C 2 Cl 2, -78 C, ii. ab 4, Et, 78%, 5.5:1 dr at C 9 ;(b)me 3 BF 4 Proton Sponge, 4 Å M.S., C 2 Cl 2, 79% (single epimer) plus C 9 epimer (15%), (c) i. s 4,M,ii.aI 4, 80%; (d) L-Selectride, TF, -90 to -60 C, 82% (single epimer) plus C 5 epimer (10%); (e) TBAF, TF, 92%; (f) TBSTf, 2,6-lutidine, C 2 Cl 2, 89% Bn TBS Kopecky, D. J.; Rychnovsky, S. D. J. Am. Chem. Soc. 2001, 123, 8420
17 Me 1 Rychnovsky s Synthesis Me Bn Me TBS TBS g-j Me TBS TBS TBS k-n Me o-p Me AC (g) 2,Pd() 2, EtAc, 96%; (h) Swern, 94%; (i) Me 2 AlCl, Me 3 SnCCC 2 C(C 3 ) 2, PhC 3, -78 C, 80%, 3.5:1 dr at C ; (j) Red-Al, Et 2, 60% (single epimer) plus recovered SM and C epimer; (k) Ac 2, DMAP, pyridine, C 2 Cl 2, 89%; (l) eutral Al 2 3, hexanes, 96%; (m) Swern, 97%; (n) acl 2,a 2 P 4, 2-methyl-2-butene, 71%; (o) i. K 2 C 3, Me, ii. Cl 3 C 6 2 CCl, Et 3, DMAP, C 6 6, 23 C, 56%; (p) F. pyridine, TF, 96% Kopecky, D. J.; Rychnovsky, S. D. J. Am. Chem. Soc. 2001, 123, 8420
18 Me 1 Kozmin s Synthesis Me Selective ydrosilyation 1,5 Anti Aldol Prins Me Macrolactolization Wang, Y.; Janjic, J.; Kozmin, S. A. J. Am. Chem. Soc. 2002, 124, 13670
19 Me 1 Kozmin s Synthesis Me Me PPTS, toluene 92% CF 3 C 2, 5 C Li, TF- 2 77% Bn BnC()CCl 5 3 Tf (cat) 71% 7 3 Wang, Y.; Janjic, J.; Kozmin, S. A. J. Am. Chem. Soc. 2002, 124, 13670
20 Me 1 Kozmin s Synthesis Me 1. cyclohexyl amine MgS 4 2. Et 2 Li 74% Br Br Br 1. C 2 C 2, Ts(cat) 2. n-buli, TF, -78 o C; DMF 51% C Wang, Y.; Janjic, J.; Kozmin, S. A. J. Am. Chem. Soc. 2002, 124, 13670
21 Me 1 Kozmin s Synthesis Me Bn Cy 2 BCl, Et 3, -78 o C C 74% dr >95:5 Bn SmI 2 (30 mol%) C 3 C, TF, -5 o C 92% Ac dr >95:5 Bn MeTf, 2, 6-di-t- Bupyridine 71% LiAl 4, ether, -78 o C, 86% Me Bn Wang, Y.; Janjic, J.; Kozmin, S. A. J. Am. Chem. Soc. 2002, 124, 13670
22 Me 1 Kozmin s Synthesis Me Me Bn (Me 2 Si) 2 2 PtCl 6, 50 o C dr: 87:13 Si Me Bn TBAF, DMF, 70 o C, 54% 15 Me 1 Bn Me Bn Wang, Y.; Janjic, J.; Kozmin, S. A. J. Am. Chem. Soc. 2002, 124, 13670
23 Me 1 Kozmin s Synthesis Me Me 1. TF- 2, + ; Bn Ac 2, Py, 83% 2. ZnCl 2, C 2 Cl 2 TMS 80% Me Bn 1. L-Selectride TF -78 o C 65% 2. s 4 (cat) M, t-bu- 2 77% 3. Red-Al, ether 20 o C, 18h, 78% Me Bn Pb(Ac) 4 Et Me Bn Me 18h, 20 o C 92% Me Bn Wang, Y.; Janjic, J.; Kozmin, S. A. J. Am. Chem. Soc. 2002, 124, 13670
24 Me 1 Kozmin s Synthesis Me Me Me 1. n-buli, TIPSTf 2. n-buli, TsC, -78 o C TIPS C 2 Me Me 1. Et 2 Li, MPA, 86% 2. KMDS, 75% Me 3. Li 89% P C2 CF 3 C 2 CF 3 Me 1. 2, Pd/CaC 3 2. Et 3 BLi, 0 o C 3. CBr 4, PPh 3 51% Me 1. Rh 2 (Ac) 4 5 mol% C Me Me 2. F 2 Br Me C Wang, Y.; Janjic, J.; Kozmin, S. A. J. Am. Chem. Soc. 2002, 124, 13670
25 Me 1 Kozmin s Synthesis Me Me Me Bn 1. PCC, C 2 Cl 2 85% 2. DDQ, C 2 Cl 2 99% Me Me + Me Me Me DIAD, PPh 3 Benzene 20 o C 78% Me C Wang, Y.; Janjic, J.; Kozmin, S. A. J. Am. Chem. Soc. 2002, 124, 13670
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