Recent Advances in the Synthesis of Stemona Alkaloids

Natural Product Communications

Volumn 10, Issue 6, 2015, Pages

  Liu, Xiao Yu ^a   Wang, Feng Peng ^a  

^a SICHUAN UNIVERSITY   (China)

Author keywords

Formal synthesis; Stemona alkaloid; Stemonaceae; Total synthesis

Indexed keywords

ALKALOID; HERBACEOUS AGENT;

CHEMICAL STRUCTURE; CHEMISTRY; STEMONACEAE; SYNTHESIS;

ALKALOIDS; DRUGS, CHINESE HERBAL; MOLECULAR STRUCTURE; STEMONACEAE;

EID: 84970973654     PISSN: 1934578X     EISSN: 15559475     Source Type: Journal    
DOI: 10.1177/1934578X1501000674     Document Type: Article

References (50)

1. Pilli RA, Rosso GB, Oliveira MCF. (2005) The Stemona alkaloids. In The Alkaloids. Vol. 62, Cordell GA. (Eds). Elsevier Science, New York, 77.
2. Wang FP, Chen QH. (2014) Stemona alkaloids: biosynthesis, classification, and biogenetic relationships. Natural Product Communications, 9, 1809–1822.
3. Pilli RA, Rosso GB, Oliveira MCF. (2000) Recent progress in the Stemona alkaloids. Natural Product Reports, 17, 117–127.
4. Pilli RA, Rosso GB, Oliveira MCF. (2010) The chemistry of Stemona alkaloids: an update. Natural Product Reports, 27, 1908–1937.
5. Greger H., (2006) Structural relationships, distribution and biological activities of Stemona alkaloids. Planta Medica, 72, 99–113.
6. Seger C, Mereiter K, Kaltenegger E, Pacher T, Greger H, Hofer O., (2004) Two pyrrolo[1,2-a] azepine type alkaloids from Stemona collinsae Craib: structure elucidation, relationship to asparagamine A, and a new biogenetic concept of their formation. Chemistry & Biodiversity, 1, 265–279.
7. Kaltenegger E, Brem B, Mereiter K, Kalchhauser H, Kahlig H, Hofer O, Vajrodaya S, Greger H., (2003) Insecticidal pyrido[1, 2-a]azepine alkaloids and related derivatives from Stemona species. Phytochemistry, 63, 803–816.
8. Greger H, Schinner K, Vajrodaya S, Brecker L, Hofer O., (2009) Pandanus alkaloids in Stemonaceae: finding of a plausible biogenetic origin of Stemona alkaloids. Journal of Natural Products, 72, 1708–1711.
9. Kongkiatpaiboon S, Schinnerl J S., Felsinger S, Keeratinijakal V, Vajrodaya S, Gritsanapan W, Brecker L, Greger H., (2011) Structural relationships of Stemona alkaloids: assessment of species-specific accumulation trends for exploiting their biological activities. Journal of Natural Products, 74, 1931–1938.
10. Alibés R, Figueredo M., (2009) Strategies for the synthesis of Stemona alkaloids. European Journal of Organic Chemistry, 2424–2435.
11. Chen J, Chen J, Xie Y, Liu N, Liu D, Zhang H., (2013) Research progress on the synthesis of stenine. Chinese Journal of Organic Chemistry, 33, 1186–1194.
12. Wang Y, Zhu L, Zhang Y, Hong R., (2011) Bioinspired and concise synthesis of (±)-stemoamide. Angewandte Chemie International Edition, 50, 2787–2790.
13. Yoneda E, Kaneko T, Zhang SW, Onitsuka K, Takahashi S., (2000) Ruthenium-catalyzed cyclic carbonylation of allenyl alcohols. Selective synthesis of γ- and δ-lactones. Organic Letters, 2, 441–443.
14. Mi X, Wang Y, Zhu L, Wang R, Hong R., (2012) Enantioselective synthesis of (–)-stemoamide. Synthesis, 44, 3432–3440.
15. Muňoz-Bascón J, Hernández-Cervantes C, Padial NM, Álvarez-Corral M, Rosales A, Rodríguez-García I, Oltra JE. (2014) Ti-Catalyzed straightforward synthesis of exocyclic allenes. Chemistry - A European Journal, 20, 801–810.
16. Li Z, Zhang L, Qiu FG. (2014) A concise stereocontrolled total synthesis of (–)-stemoamide. Asian Journal of Organic Chemistry, 3, 52–54.
17. Wipf P, Kim Y, Goldstein DM. (1995) Asymmetric total synthesis of the Stemona alkaloid (–)-stenine. Journal of the American Chemical Society, 117, 11106–11112.
18. Wipf P, Li W., (1999) Formation of nine-membered lactams by oxidative ring expansion of 4-hydroxyhydroindoles: abiomimetic approach toward the tuberostemonone ring system? The Journal of Organic Chemistry, 64, 4576–4577.
19. Wipf P, Rector SR, Takahashi H., (2002) Total synthesis of (–)-tuberostemonine. Journal of the American Chemical Society, 124, 14848–14849.
20. Wipf P, Spencer SR. (2005) Asymmetric total syntheses of tuberostemonine, didehydrotuberostemonine, and 13-epituberostemonine. Journal of the American Chemical Society, 127, 225–235.
21. Hoye AT, Wipf P., (2011) Total synthesis of (–)-sessilifoliamide C and (–)-8-epi-stemoamide. Organic Letters, 13, 2634–2637.
22. Zheng X, Dai XJ, Yuan HQ, Ye CX, Ma J, Huang P., (2013) Umpolung of hemiaminals: titanocene-catalyzed dehydroxylative radical coupling reactions with activated alkenes. Angewandte Chemie International Edition, 52, 3494–3498.
23. Hitotsuyanagi Y, Takada E, Fukaya H, Takeya K., (2008) Sessilifoliamine A and sessilifoliamide J: new alkaloids from Stemona sessilifolia. Tetrahedron Letters, 49, 7376–7379.
24. Tuo SC, Ye JL, Wang AE, Huang SY, Huang PQ. (2011) Concise asymmetric total synthesis of 9-epi-sessilifoliamide J. Organic Letters, 13, 5270–5273.
25. Liu XK, Ye JL, Ruan YP, Li YX, Huang PQ. (2013) Total synthesis of (–)-sessilifoliamide J. The Journal of Organic Chemistry, 78, 35–41.
26. Corey EJ, Zheng GZ. (1997) Catalytic reactions of samarium (II) iodide. Tetrahedron Letters, 38, 2045–2048.
27. Hanessian S, McNaughton-Smith G., (1996) A versatile synthesis of a β-turn peptidomimetic scaffold: an approach towards a designed model antagonist of the tachykinin NK-2 receptor. Bioorganic & Medicinal Chemistry Letters, 6, 1567–1572.
28. Bardají N, Sánchez-Izquierdo F, Alibés R, Font J, Busqué F, Figueredo M., (2012) Flexible approach to Stemona alkaloids: total syntheses of (–)-stemospironine and three new diastereoisomeric analogs. Organic Letters, 14, 4854–4857.
29. Sánchez-Izquierdo F, Blanco P, Busqué F, Alibés R, de March P, Figueredo M, Font J, Parella T., (2007) Total synthesis of the putative structure of stemonidine: the definitive proof of misassignment. Organic Letters, 9, 1769–1772.
30. Fu J, Shen H, Chang Y, Li C, Gong J, Yang Z., (2014) Concise stereoselective synthesis of oxaspirocycles with 1-tosyl-1,2,3-triazoles: application to the total syntheses of (±)-tuberostemospiroline and (±)-stemona-lactam R. Chemistry - A European Journal, 20, 12881–12888.
31. Chattopadhyay B, Gevorgyan V., (2012) Transition-metal-catalyzed denitrogenative transannulation: converting triazoles into other heterocyclic systems. Angewandte Chemie International Edition, 51, 862–872.
32. Schulte ML, Turlington ML, Phatak SS, Harp JM, Stauffer SR, Lindsley CW. (2013) Total synthesis of stemaphylline N-oxide and related C9a-epimeric analogues. Chemistry - A European Journal, 19, 11847–11852.
33. Fadeyi OO, Senter TJ, Hahn KN, Lindsley CW. (2012) A versatile enantioselective synthesis of azabicyclic ring systems: a concise total synthesis of (+)-grandisine D and unnatural analogues. Chemistry - A European Journal, 18, 5826–5831.
34. Zhao YM, Gu P, Tu YQ, Fan CA, Zhang Q., (2008) An efficient total synthesis of (±)-stemonamine. Organic Letters, 10, 1763–1766.
35. Zhao YM, Gu P, Zhang HJ, Zhang QW, Fan CA, Tu YQ, Zhang FM. (2009) Formal syntheses of (±)-stemonamine and (±)-cephalotaxine. The Journal of Organic Chemistry, 74, 3211–3213.
36. Chen ZH, Zhang YQ, Chen ZM, Tu YQ, Zhang FM. (2011) Total synthesis of (±)-maistemonine and (±)-stemonamide. Chemical Communications, 47, 1836–1838.
37. Chen ZH, Chen ZM, Zhang YQ, Tu YQ, Zhang FM. (2011) Total synthesis of (±)-maistemonine, (±)-stemonamide, and (±)-isomaistemonine. The Journal of Organic Chemistry, 76, 10173–10186.
38. Taniguchi T, Ishibashi H., (2008) Total synthesis of (±)-stemonamide, (±)-isostemonamide, (±)-stemonamine, and (±)-isostemonamine using a radical cascade. Tetrahedron, 64, 8773–8779.
39. Hirst GC, Howard PN, Overman LE. (1989) Stereocontrolled construction of carbocyclic rings by sequential cationic cyclization-pinacol rearrangements. Journal of the American Chemical Society, 111, 1514–1515.
40. Chen ZH, Tu YQ, Zhang SY, Zhang FM. (2011) Development of the intramolecular Prins cyclization/Schmidt reaction for the construction of the azaspiro[4,4]nonane: application to the formal synthesis of(±)-stemonamine. Organic Letters, 13, 724–727.
41. Kim C, Kang S, Rhee YH. (2014) Synthesis of the tricyclic core in stemonamine alkaloids via one-pot gold(I)-catalyzed cyclization and Schmidt rearrangement: formal synthesis of (±)-stemonamine. The Journal of Organic Chemistry, 79, 11119–11124.
42. Kende AS, Smalley TL, Jr., Huang H., (1999) Total synthesis of (±)-isostemofoline. Journal of the American Chemical Society, 121, 7431–7432.
43. Brüggemann M, McDonald AI, Overman LE, Rosen MD, Schwink L, Scott JP. (2003) Total synthesis of (±)-didehydrostemofoline (asparagamine A) and (±)-isodidehydrostemofoline. Journal of the American Chemical Society, 125, 15284–15285.
44. Fang C, Shanahan CS, Paull DH, Martin SF. (2012) Enantioselective formal total syntheses of didehydrostemofoline and isodidehydrostemofoline through a catalytic dipolar cycloaddition cascade. Angewandte Chemie International Edition, 51, 10596–10599.
45. During the evaluation of the manuscript, a paper concerning the synthesis of another two stemofoline-type alkaloids was published, see: Huang PQ, Huang SY, Gao LH, Mao ZY, Chang Z, Wang AE. (2015) Enantioselective total synthesis of (+)-methoxystemofoline and (+)-isomethoxystemofoline. Chemical Communications, 51, 4576–4578.
46. Uyeo S, Irie H, Harada H., (1967) The structure of stenine, a new alkaloid occurring in Stemona tuberosa. Chemical and Pharmaceutical Bulletin, 15, 768–770.
47. Chen J, Chen J, Xie Y, Zhang HB. (2012) Enantioselective total synthesis of (–)-stenine. Angewandte Chemie International Edition, 51, 1024–1027.
48. Fujioka H, Nakahara K, Kotoku N, Ohba Y, Nagatomi Y, Wang TL, Sawama Y, Murai K, Hirano K, Oki T, Wakamatsu S, Kita Y., (2012) Asymmetric total synthesis of (–)-stenine and 9a-epi-stenine. Chemistry - A European Journal, 18, 13861–13870.
49. 2 catalyzed enantioselective Michael additions of 1,3-dicarbonyl compounds to conjugated nitroalkenes. Journal of the American Chemical Society, 127, 9958–9959.
50. Fujioka H, Kotoku N, Sawama Y, Kitagawa H, Ohba Y, Wang TL, Nagatomi Y, Kita Y., (2005) Asymmetric synthesis by the intramolecular haloetherification reaction of ene acetal: discrimination of prochiral dienes in cyclohexane systems. Chemical and Pharmaceutical Bulletin, 53, 952–957.