The stereoselective total synthesis of aculeatin A and B via prins cyclization

Synthesis

Volumn , Issue 3, 2010, Pages 431-436

  Yadav, J S ^a   Thrimurtulu, N ^a   Venkatesh, M ^a   Prasad, A R ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

Aculeatins; Morpholine amide; PIFA mediated oxidative spirocyclization; Prins cyclization

Indexed keywords

ACULEATINS; MORPHOLINES; NATURAL PRODUCT SYNTHESIS; PRINS CYCLIZATION; SPIROCYCLIZATION; STEREO-SELECTIVE; TOTAL SYNTHESIS;

ACETYLENE; AMIDES; ISOMERS; STEREOSELECTIVITY;

CYCLIZATION;

ACULEATIN A; ACULEATIN B; ALKYNE DERIVATIVE; AMIDE; MORPHOLINE DERIVATIVE; NATURAL PRODUCT; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; OXIDATION; PRINS CYCLIZATION; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 75849158404     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0029-1217144     Document Type: Article

References (51)

1. Heilmann J, Mayr S, Brun R, Rali T, Sticher O, Helv. Chim. Acta 2000 83 2939
2. Heilmann J, Brun R, Mayr S, Rali T, Sticher O, Phytochemistry 2001 57 1281
3. Chin Y, Salim A A., Su B, Mi Q, Chai H, Riswan S K., Leonardus B S., Ruskandi A, Farnsworth N R., Swanson S M., Kinghorn A D., J. Nat. Prod. 2008 71 390
4. Peuchmaur M, Saïdani N, Botte C, Marechal E, Vial H, Wong D Y., J. Med. Chem. 2008 51 4870
5. Wong Y S., Chem. Commun. 2002 686
6. Falomir E, Alvarez-Bercedo P, Carda M, Marco J A., Tetrahedron Lett. 2005 46 8407
7. Baldwin J E., Adlington R M., Sham V W. W., Marquez R, Bulger P G., Tetrahedron 2005 61 2353
8. Alvarez-Bercedo P, Falomir E, Carda M, Marco J A., Tetrahedron 2006 62 9641
9. Euchmaur M, Wong Y S., J. Org. Chem. 2007 72 5374
10. Chandrasekhar S, Rambabu C, Shyamsunder T, Tetrahedron Lett. 2007 48 4683
11. Ramana C V., Srinivas B, J. Org. Chem. 2008 73 3915
12. Zhen Z, Gao J, Wu S, J. Org. Chem. 2008 73 7310
13. Suresh V, Selvam J, Rajesh K, Venkateswarlu Y, Tetrahedron: Asymmetry 2008 19 1509
14. For the Prins cyclization, see for example:, Barry C St J., Crosby S R., Harding J R., Hughes R A., King C D., Parker G D., Willis C L., Org. Lett. 2003 5 2429
15. Yang X.-F, Mague J T., Li C.-J, J. Org. Chem. 2001 66 739
16. Aubele D L., Wan S, Floreancig P E., Angew. Chem. Int. Ed. 2005 44 3485
17. Barry C S., Bushby N, Harding J R., Willis C S., Org. Lett. 2005 7 2683
18. Cossey K N., Funk R L., J. Am. Chem. Soc. 2004 126 12216
19. Crosby S R., Harding J R., King C D., Parker G D., Willis C L., Org. Lett. 2002 4 3407
20. Marumoto S, Jaber J J., Vitale J P., Rychnovsky S D., Org. Lett. 2002 4 3919
21. Kozmin S A., Org. Lett. 2001 3 755
22. Jaber J J., Mitsui K, Rychnovsky S D., J. Org. Chem. 2001 66 4679
23. Kopecky D J., Rychnovsky S D., J.Am. Chem. Soc. 2001 123 8420
24. Rychnovsky S D., Thomas C R., Org. Lett. 2000 2 1217
25. Rychnovsky S D., Yang G, Hu Y, Khire U R., J. Org. Chem. 1997 62 3022
26. Su Q, Panek J S., J. Am. Chem. Soc. 2004 126 2425
27. Yadav J S., Reddy B V. S., Sekhar K C., Gunasekar D, Synthesis 2001 885
28. Yadav J S., Reddy B V. S., Reddy M S., Niranjan N, J. Mol. Catal. A: Chem. 2004 210 99
29. Yadav J S., Reddy B V. S., Reddy M S., Niranjan N, Prasad A R., Eur. J. Org. Chem. 2003 1779
30. Yadav J S., Reddy M S., Rao P P., Prasad A R., Tetrahedron Lett. 2006 47 4397
31. Yadav J S., Reddy M S., Prasad A R., Tetrahedron Lett. 2006 47 4937
32. Yadav J S., Reddy M S., Prasad A R., Tetrahedron Lett. 2005 46 2133
33. Yadav J S., Reddy M S., Prasad A R., Tetrahedron Lett. 2006 47 4995
34. Yadav J S., Reddy M S., Rao P P., Prasad A R., Synlett 2007 2049
35. Yadav J S., Rao P P., Reddy M S., Rao N V., Prasad A R., Tetrahedron Lett. 2007 48 1469
36. Yadav J S., Kumar N N., Reddy M S., Prasad A R., Tetrahedron 2006 63 2689
37. Rao A V. R., Reddy E R., Joshi B V., Yadav J S., Tetrahedron Lett. 1987 28 6497
38. Yadav J S., SridharReddy M, Rao P P., Prasad A R., Synlett 2049 2007
39. Yadav J S., Issana A, Gayathri K U., Rao N V., Prasad A R., Synthesis 2008 3945
40. Bonini C, Chiummiento L, Lopardo M T., Pullex M, Colobert F, Solladie G, Tetrahedron Lett. 2003 44 2695
41. Yadav J S., Thrimurtulu N, Gayathri U K., SubbaReddy B V., Prasad A R., Tetrahedron Lett. 2008 49 6617
42. Yadav J S., SridharReddy M, PurushothamaRao P, Prasad A R., Tetrahedron Lett. 2006 47 4397
43. Mitsunobu O, Synthesis 1981 1
44. Raghavan S, RamakrishnaReddy S, Tetrahedron Lett. 2004 45 5593
45. Furst M, Ruck-Braun K, Synlett 2002 1991
46. Martin R, Romea P, Tey C, Urpi F, Vilarrasa J, Synlett 1997 1414
47. For a review on hypervalent iodine compounds, see:, Zhadankin V V., Stang P J., Chem. Rev. 2002 102 2523 For more recent developments, see:
48. Moriaty R M., J. Org. Chem. 2005 70 2893
49. Wirth T, Angew. Chem. Int. Ed. 2005 44 3656
50. For oxidation of phenolic compounds with hypervalent iodine reagents, see:, Moriarty R M., Prakash O, Org. React. 2001 57 327
51. Rodriguez S, Wipf P, Synthesis 2004 767