Total Synthesis of (-)-Anominine
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1 Total Synthesis of (-)-Anominine Ben Bradshaw, Gorka Etxbarria-Jardí and Josep Bonjoch* Laboratori de Química rgànica, Facultat de Farmàci, Universitat de Barcelona, Barcelona, Spain J. Am. Chem. Soc. 2010, 132, H Xueling Mi Wipf Group Current Literature May 22, 2010 Xueling Wipf Group Page 1 of 9 5/23/2010
2 isolated by J. B. Gloer from the sclerotia of the fungus Aspergillus nomius (NRRL 13137) in 1989 (along with aspernomine, 14-hydroxypaspalinine, 14-[(N,N-dimethylvalyl)oxy]paspalinine) structure was identified through NMR decoupling studies and by spectral comparison with aflavinines biogenetically related to the aflavinines A. nomius is close related to the common fungi A. flavus and A. parasiticus (both can selectively allocate antisectan aflavinine derivatives to their sclerotia) exhibit potent activity against crop pest Heliothis zea in controlled feeding experiments (causing 40% mortality and a 97% reduction in weight relative to controls when incorporated into a standard test diet at 100 ppm dry weight) ring structure: 2 quaternary C at the decalin ring junction and 5 stereocenters all arranged in a cis configuration Aflavinine (R=H, H) Gloer, J. B., Rinderknecht, B. L. Wicklow, D. T., Dowd, P. F. J. rg. Chem. 1989, 54, ; Gloer, J. B. Acc. Chem. Res. 1995, 28, ; Xueling Wipf Group Page 2 of 9 5/23/2010
3 Synthesis of 3-Desmethylaflavinine H Br, Mg 3, -78 o C, then DMS Li, -78 o C CuI, DMS Et 2 quenched with CCl 72% H, PTSA 88% then then HCl N + Cl - 2 N () 2 P C 2, NaH Br 30-35% over 3 steps E:Z = 2:3 2 C Br 2 N 1) mcpba 2) TMS, Li [2+2+2] 25% 2 C Br H LiAlH 4, 55% then Mn 2, 80% H CH(Li)Si 3 then KH H HCl 4 then Ph 2 24% HN H 3-Desmethylaflavinine Danishefsky, S., Chackalamannil, S., Harrison, P., Silvestri, M., Cole, P. J. Am. Chem. Soc. 1985, 107, Xueling Wipf Group Page 3 of 9 5/23/2010
4 H Previous Attempt of framework synthesis of Anominine Li, CuI,Et 2 85% Wieland-Mischer Ketone TsH 99% Ph 3 P + CH 3 Br - tbuk 95% 1) BH 3. THF 2) H 2 2, NaH 60% (4:1) H 1) MsCl, Et 3 N 2) LiBHEt 3, THF 3) acid quench (10% HCl) 74% over 3 steps IBX, TsH DMS 1) LiHMDS, THF N 2 2) N I 1) H2/Pd, H 2) mcpba 71% 69% 18%, 11 steps indole, Bi(Tf) 3 CH 3 CN 93%, 1:2 KF, EtH rfx 98% Bradshaw, B., Etxebarria-Jardi, G., Bonjoch, J. rg. Biomol. Chem. 2008, 6, ; Diaz, S., Cuesta, J., Gonzalez, A., Bonjoch, J. J. rg. Chem. 2003, 68, ; Paquette, L. A., Wang, T. Z., Philippo, C. M. G., Wang, S. J. Am. Chem. Soc. 1994, 116, Ph 3 P=CH 2 Xueling Wipf Group Page 4 of 9 5/23/ %
5 Retrosynthetic Analysis selective alkene cross metathesis unusual selenoxide [2,3] sigmatropic rearrangement H (-)-Anominine ZrCl 4 coupling H highly efficient WMK synthesis solvent-free 94-97% ee large scale Xueling Wipf Group Page 5 of 9 5/23/2010
6 rganocatalyzed Asymmetric Synthesis of 3 a. MVK, Et 3 N (1 mol%) b. solvent-free Ts (1 mol%) 91% overall, 94% ee 79% [up to 20 gm scale] PhC 2 H (2.5 mol%) c. 2 CuLi, Et 2 The Wieland-Miescher Ketone Synthesis Et 3 N (1 mol%) r.t., 3 h, 96% rganocatalyst (2.5 mol%) PhC 2 H (1 mol%) solvent-free 93%, 97% ee Xueling Wipf Group Page 6 of 9 5/23/2010
7 Synthesis of Key Intermediate 9 d. 2-ethyl-1,3-dioxolane, TsH then Ph 3 PCH 3 Br, tbuk, Tol. then TsH, acetone e. IBX, TsH DMS, 70 o C 85% overall 65% f. LiHMDS, CH 2 =N + 2 I - then mcpba g, L-Selectride, then LiHMDS AcH quench 64% overall h. NaBH 4, CeCl 3 i. PBu 3, o-n 2 -C 6 H 4 SeCN ArSe 7 8 j. mcpba, DCM H 2, -78 o C C 6H 4 N 2 Se epimerization at Se via hydrate: fast [2,3]-s then NaEt H 70% overall [gram scale] hindered rotation around C-Se bond 9 Xueling Wipf Group Page 7 of 9 5/23/2010
8 Completion of the Synthesis of (-)-Anominine Ac H k. TESTf, 2,6-lutidine (83%) l. 9-BBN, then H 2 2, NaH (68%) TES H m. H 2, Pd/C, H n. Ac 2, Et 3 N TES 68% over 2 steps Ac o. Se 2, μw, 30 min (49%) p. DMP, r.t. (81%) TES q. indole, ZrCl 4 r. KF, EtH, rfx, 24 h TES H 84% over 2 steps s. TPAP, NM t. Ph 3 P=CH 2, THF TES u. Grubbs II, DMC, r.t., 48 h (CH 3 ) 2 C=CHCH 3 v. TBAF, THF, rfx H 53% over 2 steps 80% over 2 steps 14 (-)-anominine (1) Xueling Wipf Group Page 8 of 9 NMR data: identical [α] D = (c 0.3, H) [α] D = (c 0.85, H) (natural (+)-Anominine) 5/23/2010
9 Summary 1. The first synthesis of anominine has been achieved 2. The absolute configuration was established 3. New highly efficient method for the synthesis of Wieland-Miescher ketone compounds (high yield and ee, small catalyst loading amount, scalable) 4. Several chemoselective transformations controlled by the structurally congested nature of the bicyclic core 5. pen the way for other related natural products from Aspergillus spp. H Xueling Wipf Group Page 9 of 9 5/23/2010
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