Asymmetric total synthesis of (-)-lingzhiol via a Rh-catalysed [3+2] cycloaddition

Nature Communications

Volumn 5, Issue , 2014, Pages

  Long, Rong ^a,b   Huang, Jun ^a,b   Shao, Wenbin ^a,b   Liu, Song ^c   Lan, Yu ^c   Gong, Jianxian ^a,b   Yang, Zhen ^a,b,d  

^a PEKING UNIVERSITY   (China)

^b Peking University   (China)

^c CHONGQING UNIVERSITY   (China)

^d OCEAN UNIVERSITY OF CHINA   (China)

Author keywords

[No Author keywords available]

Indexed keywords

LINGZHIOL; NATURAL PRODUCT; RHODIUM; UNCLASSIFIED DRUG; CARBON; PHOSPHINE DERIVATIVE; TERPENE;

ASYMMETRY; BIOACTIVITY; QUATERNARY; REACTION KINETICS; RHODIUM;

ALKYLATION; ANNULATION REACTION; ARTICLE; ASYMMETRIC SYNTHESIS; CATALYSIS; CHIRALITY; CONTROLLED STUDY; CYCLOADDITION; DENSITY FUNCTIONAL THEORY; DIABETIC NEPHROPATHY; DIASTEREOISOMER; DRUG SYNTHESIS; ENANTIOMER; GANODERMA LUCIDUM; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MICHAEL ADDITION; NONHUMAN; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION; X RAY CRYSTALLOGRAPHY; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; CYCLIZATION; ENZYME SPECIFICITY; PROCEDURES; STEREOISOMERISM; SYNTHESIS;

CARBON; CATALYSIS; CYCLIZATION; CYCLOADDITION REACTION; MODELS, MOLECULAR; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; PHOSPHINES; RHODIUM; STEREOISOMERISM; SUBSTRATE SPECIFICITY; TERPENES;

EID: 84923351203     PISSN: None     EISSN: 20411723     Source Type: Journal    
DOI: 10.1038/ncomms6707     Document Type: Article

References (68)

1. Groweiss, A. et al. Subergorgic acid, a novel tricyclopentanoid cardiotoxin from the pacific gorgonian coral. Tetrahedron Lett. 26, 2379-2382 (1985).
2. Anke, T. et al. Crinipellins, the first natural products with a tetraquinane skeleton. Angew. Chem. Int. Ed. 24, 709-711 (1986).
3. Kaneda, M., Takahashi, R., Iitaka, Y. & Shibata, S. Retigeranic acid, a novel sesterterpene isolated from the lichens of lobaria retigera group. Tetrahedron Lett. 13, 4609-4612 (1972).
4. Yan, Y.-M. et al. Lingzhiols, unprecedented rotary door-shaped meroterpenoids as potent and selective inhibitors of p-Smad3 from Ganoderma lucidum. Org. Lett. 15, 5488-5491 (2013).
5. Dong, L.-B. et al. Isopalhinine A, a unique pentacyclic lycopodium alkaloid from palhinhaea cernua. Org. Lett. 15, 3570-3573 (2013).
6. Boeckman, Jr R. K., Blum, D. M., Arnold, E. U. & Clardy, J. The structure of gascardic acid from an X-ray diffraction study. Tetrahedron. Lett. 20, 4609-4694 (1979).
7. Hog, D. T., Mayer, P. & Trauner, D. A unified approach to trans-hydrindane sesterterpenoids. J. Org. Chem. 77, 5838-5843 (2012).
8. Steven, A. & Overman, L. E. Total synthesis of complex cyclotryptamine alkaloids: Stereocontrolled construction of quaternary carbon stereocenters. Angew. Chem. Int. Ed. 46, 5488-5508 (2007).
9. Nicolaou, K. C., Vassilikogiannakis, G., Mägerlein, W. & Kranich, R. Total synthesis of colombiasin A. Angew. Chem. Int. Ed. 40, 2482-2486 (2001).
10. Birman, V. B. & Danishefsky, S. J. The total synthesis of (±)-merrilactone A. J. Am. Chem. Soc. 124, 2080-2081 (2002).
11. Overman, L. E., Larrow, J. F., Stearns, B. A. & Vance, J. M. Enantioselective construction of vicinal stereogenic quaternary centers by dialkylation: Practical total syntheses of (±)-and meso-chimonanthine. Angew. Chem. Int. Ed. 39, 213-215 (2000).
12. Crimmins, M. T. et al. Total synthesis of (±)-ginkgolide B. J. Am. Chem. Soc. 121, 10249-10250 (1999).
13. Overman, L. E., Paone, D. V. & Stearns, B. A. Direct stereo-and enantiocontrolled synthesis of vicinal stereogenic quaternary carbon centers. Total syntheses of meso-and (-)-chimonanthine and (±)-calycanthine. J. Am. Chem. Soc. 121, 7702-7703 (1999).
14. Hatcher, J. M. & Coltart, D. M. Copper(I)-catalyzed addition of Grignard reagents to in situ-derived N-sulfonyl azoalkenes: An umpolung alkylation procedure applicable to the formation of up to three contiguous quaternary centers. J. Am. Chem. Soc. 132, 4546-4547 (2010).
15. Kikushima, K., Holder, J. C., Gatti, M. & Stoltz, B. M. Palladium-catalyzed asymmetric conjugate addition of arylboronic acids to five-, six-, and seven-membered b-substituted cyclic enones: Enantioselective construction of all-carbon quaternary stereocenters. J. Am. Chem. Soc. 133, 6902-6905 (2011).
16. Trost, B. M. & Osipov, M. Palladium-catalyzed asymmetric construction of vicinal all-carbon quaternary stereocenters and its application to the synthesis of cyclotryptamine alkaloids. Angew. Chem. Int. Ed. 52, 9176-9181 (2013).
17. Zhang, Y. & Danishefsky, S. J. Total synthesis of (±)-aplykurodinone-1: Traceless stereochemical guidance. J. Am. Chem. Soc. 132, 9567-9569 (2010).
18. Jiao, L., Lin, M. & Yu, Z.-X. Rh(I)-catalyzed intramolecular [3±2] cycloaddition reactions of 1-ene-, 1-yne-and 1-allene-vinylcyclopropanes. Chem. Commun. 46, 1059-1061 (2010).
19. Yamago, S. & Nakamura, E. Org. React. 61, 1-217 (2002).
20. Chan, D. M. T. in Comprehensive Organic Synthesis Vol. 3 (eds Trost, B. M. & Fleming, I.) 271-314 (Pergamon, 1991).
21. Becker, D. A. & Danheiser, R. L. A new synthesis of substituted azulenes. J. Am. Chem. Soc. 111, 389-391 (1989).
22. Zhang, C. & Lu, X. Phosphine-catalyzed cycloaddition of 2,3-butadienoates or 2-butynoates with electron-deficient olefins. A novel [3±2] annulation approach to cyclopentenes. J. Org. Chem. 60, 2906-2908 (1995).
23. Lu, X., Zhang, C. & Xu, Z. Reactions of electron-deficient alkynes and allenes under phosphine catalysis. Acc. Chem. Res. 34, 535-544 (2001).
24. Zhu, G. et al. Asymmetric [3±2] cycloaddition of 2,3-butadienoates with electron-deficient olefins catalyzed by novel chiral 2,5-dialkyl-7-phenylphosphabicyclo[ 2.2.1]heptanes. J. Am. Chem. Soc. 119, 3836-3837 (1997).
25. Wilson, J. E. & Fu, G. C. Synthesis of functionalized cyclopentenens through catalytic asymmetric [3±2] cycloadditions of allenes with enones. Angew. Chem. Int. Ed. 45, 1426-1429 (2006).
26. Cowen, B. J. & Miller, S. J. Enantioselective [3±2]-cycloadditions catalyzed by a protected, multifunctional phosphine-containing a-amino acid. J. Am. Chem. Soc. 129, 10988-10989 (2007).
27. Fang, Y. Q. & Jacobsen, E. N. Cooperative, highly enantioselective phosphinothiourea catalysis of imine-allene [3±2] cycloadditions. J. Am. Chem. Soc. 130, 5660-5661 (2008).
28. Voituriez, A., Panossian, A., Fleury-Br-egeot, N., Retailleau, P. & Marinetti, A. 2-Phospha[3]ferrocenophanes with planar chirality: Synthesis and use in enantioselective organocatalytic [3±2] cyclizations. J. Am. Chem. Soc. 130, 14030-14301 (2008).
29. Sampath, M. & Loh, T.-P. Highly enantio-, region-and diastereo-selective one-pot [2±3]-cycloaddition reaction via isomerization of 3-butynoates to allenoates. Chem. Sci. 1, 739-742 (2010).
30. Xiao, H. et al. Asymmetric [3±2] cycloaddition of allenoates and dual activated olefins catalyzed by simple bifunctional N-acyl aminophosphines. Angew. Chem. Int. Ed. 49, 4467-4470 (2010).
31. Fujiwara, Y. & Fu, G. C. Application of a new chiral phosphepine to the catalytic asymmetric synthesis of highly functionalized cyclopentenes that bear an array of heteroatom-substituted quaternary stereocenters. J. Am. Chem. Soc. 133, 12293-12297 (2011).
32. Zhang, X.-N. & Shi, M Phosphine-catalyzed [3±2] cycloaddition of 4,4-dicyano-2-methylenebut-3-enoates with benzyl buta-2,3-dienate and penta-3,4-dien-2-one. ACS Catal. 3, 507-512 (2013).
33. Han, X. Y., Wang, Y. Q., Zhong, F. R. & Lu, Y. X. Enantioselective [3±2] cycloaddition of allenes to acrylates catalyzed by dipeptide-derived phosphines: Facile creation of functionalized cyclopentenes containing quaternary stereogenic centers. J. Am. Chem. Soc. 133, 1726-1729 (2011).
34. Marshall, J. A., Gung, B. W. & Grachan, M. L. in Modern Allene Chemistry Vol. 2 (eds Krause, N. & Hashmi, A. S. K.) 493-592 (Wiley-VCH, 2004).
35. Krause, N. & Hoffmann-Roder, A. Synthesis of allenes with organometallic reagents. Tetrahedron 60, 11671-11694 (2004).
36. Marshall, J. A. Chiral allylic and allenic metal reagents for organic synthesis. J. Org. Chem. 72, 8153-8166 (2007).
37. Ruitenberg, K., Kleijn, H., Meijer, J., Oostveen, E. A. & Vermeer, P. Palladium(0)-promoted cross-coupling of allenylmetal compounds with aryl and vinyl iodides. A novel route to aryl-and vinyl-substituted allenes. J. Organomet. Chem. 224, 399-405 (1982).
38. Russell, C. E. & Hegedus, L. S. Palladium-catalyzed acylation of unsaturated halides by anions of enol ethers. J. Am. Chem. Soc. 105, 943-949 (1983).
39. De Graaf, W., Boersma, J., Van Koten, G. & Elsevier, C. J. Chiral induction in the synthesis of 4,4-dimethyl-1-phenylpenta-1,2-diene (1-Ph-3-t-Bu-allene) catalyzed by chiral phosphine complexes of palladium. J. Organomet. Chem. 378, 115-124 (1989).
40. Werner, H., Rappert, T., Wiedemann, R., Wolf, J. & Mahr, N. Mononuclear (allenylidene)metal complexes of a d8 system: Synthesis and molecular structure of trans-[RhCl(:C:C:CRR')(PiPr3)2]. Organometallics 13, 2721-2727 (1994).
41. Banerjee, M. & Roy, S. Rhodium(I)-catalyzed carbonyl allenylation versus propargylation via redox transmetalation across tetragonal Tin(II) oxide. Org. Lett. 6, 2137-2140 (2004).
42. Werner, H. et al. Unusual pathways for metal-assisted C-C and C-P coupling reactions using allenylidenerhodium complexes as precursors. J. Am. Chem. Soc. 124, 6966-6980 (2002).
43. Wang, J.-C., Ng, S.-S. & Krische, M. J. Catalytic diastereoselective synthesis of diquinanes from acyclic precursors. J. Am. Chem. Soc. 125, 3682-3683 (2003).
44. Jones, R. A. & Krische, M. Asymmetric Total synthesis of the iridoid b-glucoside (±)-geniposide via phosphine organocatalysis. Org. Lett. 11, 1849-1851 (2009).
45. Hayashi, S., Hirano, K., Yorimitsu, H. & Oshima, K. Synthesis of arylallenes by palladium-catalyzed retro-propargylation of homopropargyl alcohols. J. Am. Chem. Soc. 130, 5048-5049 (2008).
46. Wender, P. A. et al. Transition metal-catalyzed [5±2] cycloadditions of allenes and vinylcyclopropanes: First studies of endo-exo selectivity, chemoselectivity, relative stereochemistry, and chirality transfer. J. Am. Chem. Soc. 121, 5348-5349 (1999).
47. Wender, P. A. et al. Transition metal-catalyzed [5±2] cycloadditions with substituted cyclopropanes: First studies of regio-and stereoselectivity. J. Am. Chem. Soc. 121, 10442-10443 (1999).
48. Wender, P. A. & Christy, J. P. Rhodium(I)-catalyzed [4±2±2] cycloadditions of 1,3-dienes, alkenes, and alkynes for the synthesis of cyclooctadienes. J. Am. Chem. Soc. 128, 5354-5355 (2006).
49. Marshall, J. A. & Robinson, E. D. A mild method for the synthesis of furans. Application to 2,5-bridged furano macrocyclic compounds. J. Org. Chem. 55, 3450-3451 (1990).
50. Zhao, P., Incarvito, C. D. & Hartwig, J. F. Direct observation of b-aryl eliminations from Rh(I) alkoxides. J. Am. Chem. Soc. 128, 3124 (2006).
51. Zhao, P., Incarvito, C. D. & Hartwig, J. F. Carbon-oxygen bond formation between a terminal alkoxo ligand and a coordinated olefin. Evidence for olefin insertion into a rhodium alkoxide. J. Am. Chem. Soc. 128, 9642 (2006).
52. Ma, S. & Negishi, E.-I. Palladium-catalyzed cyclization of o-haloallenes. A new general route to common, medium, and large ring compounds via cyclic carbopalladation. J. Am. Chem. Soc. 117, 6345-6357 (1995).
53. Gibson, S. E., Guillo, N., Middleton, R. J., Thuilliez, A. M. & Tozer, J. Synthesis of conformationally constrained phenylalanine analogues via 7-, 8-and 9-endo Heck cyclisations. J. Chem. Soc. Perkin Trans. 1, 447-456 (1997).
54. Takasu, K., Mizutani, S., Noguchi, M., Makita, K. & Ihara, M. Stereocontrolled total synthesis of (±)-culmorin via the intramolecular double michael addition. Org. Lett. 1, 391-393 (1999).
55. Burns, A. R., McAllister, G. D., Shanahan, S. E. & Taylor, R. J. Total Synthesis and structural reassignment of (±)-dictyosphaeric acid A: A tandem intramolecular michael addition/alkene migration approach. Angew. Chem. Int. Ed. 49, 5574-5577 (2010).
56. Takasu, K., Mizutani, S., Noguchi, M., Makita, K. & Ihara, M. Total Synthesis of (±)-culmorin and (±)-longiborneol: An efficient construction of tricyclo[6.3.0.03,9]undecan-10-one by intramolecular double michael addition. J. Org. Chem. 65, 4112-4119 (2000).
57. Conia, J. M. & Le Perchec, P. The thermal cyclisation of unsaturated carbonyl compounds. Synthesis 1, 1-19 (1975).
58. Senda, T., Ogasawara, M. & Hayashi, T. Rhodium-catalyzed asymmetric 1,4-addition of organoboron reagents to 5,6-dihydro-2(1H)-pyridinones. asymmetric synthesis of 4-aryl-2-piperidinones. J. Org. Chem. 66, 6852-6856 (2001).
59. Hayashi, T., Takahashi, M., Takaya, Y. & Ogasawara, M. Catalytic cycle of rhodium-catalyzed asymmetric 1,4-addition of organoboronic acids. arylrhodium, oxa-p-allylrhodium, and hydroxorhodium intermediates. J. Am. Chem. Soc. 124, 5052-5058 (2002).
60. Sun, Z.-M. & Zhao, P. Rhodium-mediated decarboxylative conjugate addition of fluorinated benzoic acids: Stoichiometric and catalytic transformations. Angew. Chem. Int. Ed. 48, 6726-6730 (2009).
61. Peverati, R. & Truhlar, D. G. Improving the accuracy of hybrid meta-GGA density functionals by range separation. J. Phys. Chem. Lett. 2, 2810-2817 (2011).
62. Shi, F.-Q. Density functional theory study on the mechanism of Rh-catalyzed decarboxylative conjugate addition: Diffusion-and ligand-controlled selectivity toward hydrolysis or b-hydride elimination. Org. Lett. 13, 736-739 (2011).
63. Corey, E. J., Bakshi, R. K. & Shibata, S. Highly enantioselective borane reduction of ketones catalyzed by chiral oxazaborolidines mechanism and synthetic implications. J. Am. Chem. Soc. 109, 5551-5553 (1987).
64. Poulsen, T. B., Bernardi, L., Alemán, J., Overgaard, J. & Jørgensen, K. A. Organocatalytic asymmetric direct a-alkynylation of cyclic b-ketoesters. J. Am. Chem. Soc. 129, 441-449 (2007).
65. Justik, M. W. & Koser, G. F. Oxidative rearrangements of arylalkenes with [hydroxy(tosyloxy)iodo]benzene in 95% methanol: A general, regiospecific synthesis of a-aryl ketones. Tetrahedron Lett. 45, 6159-6163 (2004).
66. Gonzàlez, D. F., Brand, J. P. & Waser, J. Ethynyl-1,2-benziodoxol-3(1 H)-one (EBX): An exceptional reagent for the ethynylation of keto, cyano, and nitro esters. Chem. Eur. J. 16, 9457-9461 (2010).
67. Luche, J.-L. Lanthanides in organic chemistry. 1. Selective 1,2 reductions of conjugated ketones. J. Am. Chem. Soc. 100, 2226-2227 (1978).
68. Nomura, K., Okazaki, K., Hori, K. & Yoshii, E. Total synthesis of (±)-granaticin. J. Am. Chem. Soc. 109, 3402-3408 (1987).