RCM/PCC oxidation strategy for synthesis of functionalized cyclic α,β-unsaturated lactones: synthesis of (+)-triacetoxygoniotriol and its diastereomers

Tetrahedron

Volumn 62, Issue 48, 2006, Pages 11165-11171

  Srikanth, G S C ^a   Krishna, Urlam Murali ^a   Trivedi, Girish K ^a   Cannon, John F ^b  

^a INDIAN INSTITUTE OF TECHNOLOGY BOMBAY   (India)

^b Brigham Young University   (United States)

Author keywords

Goniotriol; RCM and PCC oxidation; Styryllactones

Indexed keywords

7 EPITRIACETOXYGONIOTRIOL; GLUCOSE; GONIOTRIOL; LACTONE; TRIACETOXYGONIOTRIOL; UNCLASSIFIED DRUG;

ARTICLE; CRYSTAL STRUCTURE; DIASTEREOISOMER; DRUG SYNTHESIS; ENANTIOMER; OXIDATION KINETICS; PRIORITY JOURNAL; RING CLOSING METATHESIS; STEREOCHEMISTRY;

EID: 33750029924     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.09.016     Document Type: Article

References (20)

1. Fang X.-P., Anderson J.E., Chang C.-J., Fanwich P.E., and McLaughlin J.L. J. Chem. Soc., Perkin Trans. 1 (1990) 1655
2. Fang X.-P., Anderson J.E., Chang C.-J., and McLaughlin J.L. J. Nat. Prod. 54 (1991) 1034
3. Fang X.-P., Anderson J.E., Chang C.-J., and McLaughlin J.L. Tetrahedron 47 (1991) 9751
4. Talapatra S.K., Goswami D., and Talapatra B. Indian J. Chem., Sect. B 24 (1985) 29
5. Shing T.K.M., and Zhou Z.-H. Tetrahedron Lett. 33 (1992) 3333
6. Shing T.K.M., Ysui H.-C., and Zhou Z.-H. J. Org. Chem. 60 (1995) 3121
7. Chen W.P., and Roberts S.M. J. Chem. Soc., Perkin Trans. 1 (1991) 103
8. Tsubuki M., Kanai K., Nagase H., and Honda T. Tetrahedron 55 (1999) 2493
9. Yang Z.-C., and Zhou W.-S. Tetrahedron 51 (1995) 1429
10. Srikanth G.S.C., Krishna U.M., and Trivedi G.K. Tetrahedron Lett. 43 (2002) 5471
11. Bonadies F., Romano D.F., and Bonini C. J. Org. Chem. 49 (1984) 1647
12. Bonadies F., and Bonini C. Synth. Commun. 18 (1988) 1573
13. Kaliappan K.P., and Kumar N. Tetrahedron 61 (2005) 7461
14. Gracza T., and Jager V. Synthesis (1994) 1359
15. 3 (Fig. 2).
16. Prakash K.R.C., and Rao P.S. Tetrahedron 49 (1993) 1505
17. 3.
18. Ramachandran P.V., Reddy M.V., and Brown H.C. J. Indian Chem. Soc. 76 (1999) 739
19. Ramachandran P.V., Reddy M.V., and Brown H.C. Tetrahedron Lett. 41 (1999) 583
20. Fustner A., and Langermman K. J. Am. Chem. Soc. 119 (1997) 9130