Enan$oselec$ve Total Synthesis of Amphidinolide F
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1 Enan$oselec$ve Total Synthesis of Amphidinolide F Subham Mahapatra and ich G. Carter regon State University Angew. Chem. nt. Ed., 2012, 51, 7948 Nicolas Millius Bern,
2 ntroduc$on isolated from the dinoflagellate Amphidinium sp in 1991 over 30 members of this family were isolated cytotoxic acmvimes amphidinolide F: 11 stereogenic centers 25- membered macrolactone 2 trans- disposed tetrahydrofuran ring systems 1,4- diketone momf highly subsmtuted diene moiety first total synthesis (confirmamon of absolute and relamve stereochemistry of the natural product) S. Mahapatra,. G. Carter, Angew. Chem. nt. Ed. 2012, 51, J. Kobayashi, M. Tsuda, M. shibashi,. Shigemori, T. Yamasu,. irota, T. Sasaki, J. An2biot. 1991, 44,
3 etrosynthesis sulfone alkylamon/ oxidamon desulfurizamon sequence EE macrolactonizamon TBS TBS TBS Piv TES 3 4 S 2 Ph EE TES 5 TBS + TBS Piv TBS 7 TBS TBS Piv S. Mahapatra,. G. Carter, Angew. Chem. nt. Ed. 2012, 51,
4 Synthesis of common intermediate 7: Ph 8 1) (ClC) 2, DMS Et 3 N, DCM, -78 ºC 2) N 2 P()(Me) 2 9 NaMe, TF 67 % (2 steps) Ph 10 1) CSA, Me 2) PivCl, Pyr, DCM then BzCl, DMAP 61 % (from 10) Bz Piv 11 TBS 12 [PdCl 2 (PPh 3 ) 2 ], Cu, Et 3 N, TF, 78 % Bz Piv AD Mix β* tbu / 2 87 %, d.r. > 20:1 Bz Piv TBS 13 TBS 14 S. Mahapatra,. G. Carter, Angew. Chem. nt. Ed. 2012, 51,
5 Gold()- Catalyzed cycliza$on of allenes: Gagosz et al. and Krause et al. A. Buzas, F. strate, F. Gagosz, rg. Le:. 2006, 8, V. Folz, N. Krause, rg. Biomol. Chem. 2007, 5,
6 Synthesis of common intermediate 7: Ph 8 1) (ClC) 2, DMS Et 3 N, DCM, -78 ºC 2) N 2 P()(Me) 2 9 NaMe, TF 67 % (2 steps) Ph 10 1) CSA, Me 2) PivCl, Pyr, DCM then BzCl, DMAP 61 % (from 10) Bz Piv 11 TBS 12 [PdCl 2 (PPh 3 ) 2 ], Cu, Et 3 N, TF, 78 % TBS 13 Bz Piv AD Mix β* tbu / 2 87 %, d.r. > 20:1 TBS 14 Bz Piv AgBF 4 (10 mol%) TBS benzene, 80 ºC Bz % Ag + P TBS Bz 16 P = 17 P = TBS Piv TBSTf 2,6-Lut, 85 % MeLi. LiBr Et 2, -78 ºC 81 % S. Mahapatra,. G. Carter, Angew. Chem. nt. Ed. 2012, 51, TBS TBS 7 Piv building block for trans- disposed furan- prcontaining natural products 15 5
7 Synthesis of subunit 6: TBS LDA, TF then DMPU TBS [(Ph 3 P) 3 hcl] TBS TBS 7 Piv Me 2 N=C % TBS Piv PhMe, 2 89 %, d.r.=10:1 TBS 20 Piv 1) NaB 4, Me, 92 % 2) m 2 C=S, PhMe 100 ºC, 91 % 3) Bu 3 Sn, ABN, PhMe, 95 ºC, 96 % TBS TBS 21 Piv 1) F. Pyr, TF, 83 % 2) DMP, Pyr, DCM 87 % TBS 22 Piv TBS 1) 27, nbuli, TF -78 ºC, then %, d.r.=3:1 2) TBSTf, 2,6-Lut., 87 % TBS 27 S. Mahapatra,. G. Carter, Angew. Chem. nt. Ed. 2012, 51,
8 Synthesis of 27: TBS TBS 1) TMS-acetylene [PdCl 2 (PPh 3 ) 2 ], Cu, Et 3 N, TF, 78 % TBS TBS [PdCl 2 (PPh 3 ) 2 ] Bu 3 Sn, TF, 72 % 2) K 2 C 3, Me, 95 % TBS TBS X 26 X = SnBu 3 27 X = 2, DCM, 70 % S. Mahapatra,. G. Carter, Angew. Chem. nt. Ed. 2012, 51,
9 Synthesis of subunit 6: TBS LDA, TF then DMPU TBS [(Ph 3 P) 3 hcl] TBS TBS 7 Piv Me 2 N=C % TBS Piv PhMe, 2 89 %, d.r.=10:1 TBS 20 Piv 1) NaB 4, Me, 92 % 2) m 2 C=S, PhMe 100 ºC, 91 % 3) Bu 3 Sn, ABN, PhMe, 95 ºC, 96 % TBS TBS 21 Piv 1) F. Pyr, TF, 83 % 2) DMP, Pyr, DCM 87 % TBS 22 Piv X 1) 27, nbuli, TF -78 ºC, then %, d.r.=3:1 2) TBSTf, 2,6-Lut., 87 % TBS TPS TBS Piv TBS TBS 23 X = TBS 6 X = 1) F. Pyr, TF, 81% 2) PPh 3, 2, m, benzene, 90 % 27 S. Mahapatra,. G. Carter, Angew. Chem. nt. Ed. 2012, 51,
10 Synthesis of subunit 5: TBS TBS 7 Piv 1) NaB 4, Me, 95 % 2) m 2 C=S, PhMe, 100 ºC, 99 % 3) Bu 3 Sn, ABN, PhMe, 90 ºC, 91 % Piv 28 TBS TBS 1) LiAl 4. Et 2, 96 % 2) (ClC) 2, DMS, Et 3 N, DCM 29 TBS TBS Bn 30 tbuli, TF, -78 ºC then aldehyde, 72 %, d.r.=1.5:1 (31:32) Bn X Y TBS TBS 31 X =, Y = 32 X =, Y = 1) EtC=C 2, PPTS (5 mol%) DCM, 94 % 2) Pd/C, 2, PA EE 33 = 34 = S 2 Ph TBS TBS 1) Ph 2 S 2, Bu 3 P TF, 78 % (2 steps) 2) TPAP, NM, MeCN, 92 % Br - 1) F. pyr, TF 0 ºC, 80 % 2) DMS, (ClC) 2, Et 3 N, DCM S 2 Ph EE 35 TBS + PBu 3 36 nbuli, TF, 97 % (2 steps) E/Z=11:1 S 2 Ph EE 37 TBS S. Mahapatra,. G. Carter, Angew. Chem. nt. Ed. 2012, 51,
11 S 2 Ph EE TBS 1) TBAF, TF 2) TESCl, DMAP Et 3 N, DCM 95 % (2 steps) S 2 Ph EE TES 37 5 S. Mahapatra,. G. Carter, Angew. Chem. nt. Ed. 2012, 51,
12 Comple$$on of the synthesis: S 2 Ph EE TES 5 LMDS, TF MPA then 6-10 ºC to T 2.5h, 74 % S 2 Ph EE TBS TBS TES TBS Piv 38 TBS TPS TBS 6 Piv LDA, DMPU, TF; Davis oxaziridine -50 to -35 ºC : 65 % (1.8:1 4:39) (94 % brsm) TBS TBS TBS EE TES DMS, (ClC) 2 Et 3 N, DCM, 83 % 4 = C 2 Piv (42 %) 39 = C 2 (23 %) 40 = C 1) LA, Et 2 2) DMS, (ClC) 2, Et 3 N, DCM, 83 % (2 steps) S. Mahapatra,. G. Carter, Angew. Chem. nt. Ed. 2012, 51,
13 EE TBS TBS TES TBS 40 NaCl 2, 2-Me-butene Na 2 P 4. 2 tbu/ 2, 85 % TBS TBS TBS 41 P = TES 42 P = EE P C 2 PPTS, Me Cl Ar = Cl ArCCl, Et 3 N PhMe/TF Cl DMAP, 65 % (2 steps) TBS TBS TBS EE 1) Ac, TF/ 2 2) DMP, Pyr, 62 % (2 steps) 3) Et 3 N. 3F, Et 3 N/MeCN 7d, 56 % 43 amphidinolide F S. Mahapatra,. G. Carter, Angew. Chem. nt. Ed. 2012, 51,
14 Conclusion first total synthesis of amphidinolide F synthemc amphidinolide F matched with the reported isolamon data ( 1 NM, 13 C NM, [α] D ) silver- catalyzed dihydrofuran formamon regioselecmve hydrostannylamon of an enyene sulfone alkylamon/ desulfurizamon sequence 13
15 End 14
16 Synthesis of star$ng material 8: 2 C C 2 (L)-(-)-malic acid 1) B 3. SMe 2, B(Me) 3 0 ºC to rt 2) PhC(Me) 2, CSA 84% Ph 8. Flögel, M. G.. Amombo,.- U. eissig, G. Zahn,. Brüdgam,. artl, Chem Eur. J. 2003, 9, B. erradon, Tetrahedron: Asymmetry 1991, 2,
17 hira- Bestmann reac$on: + N 2 P Me Me base N 2 P Me Me Me - N 2 P Me Me Me Me P N 2 Me Me Me P Me N 2 - Me Me N 2 - P - Me P Me C C - N + N N 2 16
18 Sonogashira cross- coupling: 1 X + 2 Pd (0) or Pd () (cat.) / ligand Cu()-salt (cat.) / base / solvent = aryl, alkenyl, heteroaryl X = Cl, Br,, Tf 2 =, alkyl, aryl alkenyl, Si 3 Pd-catalyst: Pd(PPh 3 ) 2 Cl 2 or Pd(PPh 3 ) 4 Cu()-salt: Cu or CuBr base: Et 3 N, (Chx) 2 N, (i-pr) 2 NEt solvent: MeCN, TF, EtAc Cu 1 1 X L n Pd () X 2 [amine base] + X - oxidative addition transmetallation CuX 2 + amine base Pd (0) or Pd () L n Pd (0) 1 L n Pd () reductive elimination 17
19 Synthesis of star$ng 24: Et 2 C C 2 Et C 3 (1.1 equiv.) Na (1.1 equiv.) reflux, Et 2 18 h 65% Et 2 C C 2 Et K (3 equiv.) Et/ 2, reflux 24 h 89% C 2 LiAl 4 (1 equiv) TF, 5 to 25 ºC, 6 h 70% Mn 2, DCM 98% Ph 3 P CC 2 Me (1 equiv.) DCM, 45 min 93% Me DBA (1.2 equiv.) DCM, -78 to 20 ºC 92% (+)-DET, Ti(i-Pr) 4 TBP, DCM mol sieves, -35 ºC 87%, 95% ee 1) TBSCl, imid. DMAP, DMF, 99% 2) Me 3 Al, DCM -78 ºC, 95%, >20:1 dr Al - + TBS TBS TBSTf, 2,6-lut. DCM, 98% TBS 24 TBS. anisch,. Brückner, Synle: 2000, 3, Baker, J. L. Castro, J. Chem. Soc. Perkin Trans. 1990, S. Mahapatra,. G. Carter, rg. Biomol. Chem. 2009, 7,
20 Synthesis of star$ng 30: Cl 3 C N Ph Bn LiAl 4, Et 2 C 2 Me Tf, DCM C 2 Me Bn PPh 3, 2, imid. Bn B. G. Vong, S. Abraham, A. X. Xiang, E. A. Theodorakis, rg. Le:. 2003, 5, J. D. White, M. Kawasaki, J. rg. Chem. 1992, 57, 5292,
21 xida$ve desulfonyla$on with Davis oxaziridine: S 2 Ph base S 2 Ph - N Ph 2 S Ph Ph S 2 Ph N - S 2 Ph + Ph N S 2 Ph SPh M. Nielsen, C. B. Jacobsen, N. olub, M. W. Paixao, K. A. Jorgensen, Angew. Chem. nt. Ed 2010, 49,
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