Total synthesis of (+)-angelmarin

Journal of Organic Chemistry

Volumn 74, Issue 14, 2009, Pages 5083-5086

  Magolan, Jakob ^a   Coster, Mark J ^a  

^a GRIFFITH UNIVERSITY   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL EQUATIONS; ENANTIOSELECTIVE TOTAL SYNTHESIS; KEY REACTIONS; OLEFIN CROSS-METATHESIS; SHI EPOXIDATION; TOTAL SYNTHESIS; UMBELLIFERONE;

OLEFINS;

SYNTHESIS (CHEMICAL);

ALKENE; ANGELMARIN; PLANT EXTRACT; UMBELLIFERONE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOSELECTIVITY; EPOXIDATION; REACTION ANALYSIS;

COUMARINS; CYCLIZATION; PLANT EXTRACTS; STEREOISOMERISM; UMBELLIFERONES;

EID: 67650346233     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo900613u     Document Type: Article

References (37)

1. (a) Vaupel, P.; Kallinowski, F.; Okunieff, P. Cancer Res. 1989, 49, 6449.
2. (b) Helmlinger, G.; Yuan, F.; Dellian, M.; Jain, R. K. Nat. Med. 1997, 3, 177.
3. (a) Izuishi, K.; Kato, K.; Ogura, T.; Kinoshita, T.; Esumi, H. Cancer Res. 2000, 60, 6201.
4. (b) Esumi, H.; Izuishi, K.; Kato, K.; Hashimoto, K.; Kurashima, Y.; Kishimoto, A.; Ogura, T.; Ozawa, T. J. Biol. Chem. 2002, 277, 32791.
5. Li, D.; Xie, K.; Wolff, R.; Abbruzzese, J. L. Lancet 2004, 363, 1049.
6. Esumi, H.; Lu, J.; Kurashima, Y.; Hanaoka, T. Cancer Sci. 2004, 95, 685.
7. (a) Lu, J.; Kunimoto, S.; Yamazaki, Y.; Kaminishi, M.; Esumi, H. Cancer Sci. 2004, 95, 547.
8. (b) Awale, S.; Nakashima, E. M. N.; Kalauni, S. K.; Tezuka, Y.; Kurashima, Y.; Lu, J.; Esumi, H.; Kadota, S. Bioorg. Med. Chem. Lett. 2006, 16, 581.
9. (c) Awale, S.; Lu, J.; Kalauni, S. K.; Kurashima, Y.; Tezuka, Y.; Kadota, S.; Esumi, H. Cancer Res. 2006, 66, 1751.
10. (d) Zaidi, S. F. H.; Awale, S.; Kalauni, S. K.; Tezuka, Y.; Esumi, H.; Kadota, S. Planta Med. 2006, 72, 1231.
11. (e) Win, N. N.; Awale, S.; Esumi, H.; Tezuka, Y.; Kadota, S. J. Nat. Prod. 2007, 70, 1582.
12. (f) Awale, S.; Li, F.; Onozuka, H.; Esumi, H.; Tezuka, Y.; Kadota, S. Bioorg. Med. Chem. 2008, 16, 181.
13. (g) Win, N. N.; Awale, S.; Esumi, H.; Tezuka, Y.; Kadota, S. Bioorg. Med. Chem. Lett. 2008, 18, 4688.
14. (h) Win, N. N.; Awale, S.; Esumi, H.; Tezuka, Y.; Kadota, S. Bioorg. Med. Chem. 2008, 16, 8653.
15. (i) Win, N. N.; Awale, S.; Esumi, H.; Tezuka, Y.; Kadota, S. Chem. Pharm. Bull. 2008, 56, 491.
16. Willette, R. E.; Soine, T. O. J. Pharm. Sci. 1964, 275.
17. For a recent review, see: Wong, O. A.; Shi, Y. Chem. Rev. 2008, 108, 3958.
18. Shipchandler, M.; Soine, T. O.; Gupta, P. K. J. Pharm. Sci. 1970, 59, 67.
19. Steck, W. Can. J. Chem. 1971, 49, 1197.
20. Bohlmann, F.; Franke, H. Chem. Ber. 1971, 104, 3229.
21. Späth, E.; Brüch, J. Ber. Dtsch. Chem. Ges. 1937, 70B, 1023.
22. (a) Hlubucek, J. R.; Ritchie, E.; Taylor, W. C. Tetrahedron Lett. 1969, 10, 1369.
23. (b) Hlubucek, J. R.; Ritchie, E.; Taylor, W. C. Chem. Ind. (London, UK) 1969, 1780.
24. The synthesis of osthenol by the same approach was also published by Murray et al. in 1970, wherein the Claisen rearrangement of neat 7 gave osthenol (4) and its 6-isoprenyl isomer, 7-demethylsuberosin, in 74% and 14% yield, respectively. (a) Murray, R. D. H.; Ballantyne, M. M.; Mathai, K. P. Tetrahedron Lett. 1970, 11, 243.
25. (b) Murray, R. D. H.; Ballantyne, M. M.; Mathai, K. P. Tetrahedron 1971, 27, 1247.
26. 3-Chloro-3-methyl-1-butyne (6) is available for $96.20 for 5 g.
27. Clarke, D. J.; Robinson, R. S. Tetrahedron 2002, 58, 2831.
28. Scholl, M.; Ding, S.; Lee, C. W.; Grubbs, R. H. Org. Lett. 1999, 1, 953.
29. Chatterjee, A. K.; Sanders, D. P.; Grubbs, R. H. Org. Lett. 2002, 4, 1939.
30. 6-DMSO.
31. Wang, Z.-X.; Tu, Y.; Frohn, M.; Zhang, J.-R.; Shi, Y. J. Am. Chem. Soc. 1997, 119, 11224.
32. The enantiomeric excess of 2 could not be determined by using chiral HPLC under standard conditions; however, polarimetry proved satisfactory, due to the large specific rotation reported for (+)-columbianetin, see ref 5b.
33. Shu, L.; Shi, Y. Tetrahedron 2001, 57, 5213.
34. Wang, Z.-X.; Shi, Y. J. Org. Chem. 1998, 63, 3099.
35. Gerstenberger, B. S.; Konopelski, J. P. J. Org. Chem. 2005, 70, 1467.
36. Srinivas, K. V. N. S.; Mahender, I.; Das, B. Synthesis 2003, 2479.
37. Synthetic 1 was obtained from 2 of 75% ee by polarimetry (Table 1, entry 8). The specific rotation for synthetic 1 is consistent with 75% ee and this value was confirmed by chiral HPLC (see the Supporting Information).