Total synthesis of 20-norsalvinorin A. 1. Preparation of a key intermediate

Journal of Organic Chemistry

Volumn 74, Issue 6, 2009, Pages 2589-2591

  Bergman, Ylva E ^a   Mulder, Roger ^b   Perlmutter, Patrick ^a  

^a MONASH UNIVERSITY   (Australia)

^b CSIRO   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

3-FURALDEHYDE; DIASTEREOSELECTIVE; DIELS-ALDER REACTIONS; EPIMERIZATION; LEWIS ACIDS; SALVINORIN A; STEREO-SELECTIVE; TOTAL SYNTHESIS;

CHEMICAL REACTIONS;

2 (FURAN 3 YL) 9 METHOXY 6A METHYL 6,6A,10A,10B TETRAHYDRO 1H BENZO[F]ISOCHROMENE 7,10(2H,4H) DIONE; 2 (FURAN 3 YL) 9 METHOXY 6A METHYL 6,6A,8,9,10A,10B HEXAHYDRO 1H BENZO[F]ISOCHROMENE 7,10(2H,4H) DIONE; 20 NORSALVINORIN A; 3 FURALDEHYDE; 9 METHOXY 6A METHYL 2 PHENYL 6,6A,10A,10B TETRAHYDRO 1H BENZO[F]ISOCHROMENE 7,10(2H,4H) DIONE; FURFURAL; KAPPA OPIATE RECEPTOR AGONIST; LEWIS ACID; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CONFORMATIONAL TRANSITION; CONJUGATE REDUCTION; DIASTEREOISOMER; DIELS ALDER REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; EPIMERIZATION; REACTION ANALYSIS; REDUCTION; STEREOCHEMISTRY; TECHNIQUE;

DITERPENES, CLERODANE; FURALDEHYDE; HETEROCYCLIC COMPOUNDS, 3-RING; STEREOISOMERISM;

EID: 64149085750     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo802623n     Document Type: Article

References (17)

1. Roth, B. L.; Baner, K.; Westkaemper, R.; Siebert, D.; Rice, K. C.; Steinberg, S.; Ernsberger, P.; Rothman, R. B. Proc. Nat. Acad. Sci. U.S.A. 2002, 99, 11934-11939.
2. Ortega, A.; Blount, J. F. J. Chem. Soc., Perkin Trans. 1 1982, 25052508.
3. Valdés, I.; Leander, J.; Butler, W. M.; Hatfield, G. M.; Paul, A. G.; Koreeda, M. J. Org. Chem. 1984, 49, 4716-4720.
4. Scheerer, J. R.; Lawrence, J. F.; Wang, G. C.; Evans, D. A. J. Am. Chem. Soc. 2007, 129, 8968-8969.
5. Nozawa, M.; Suka, Y.; Hoshi, T.; Suzuki, T.; Hagiwara, H. Org. Lett. 2008, 10, 1365-1368.
6. Lingham, A. R.; Hügel, H. M.; Rook, T. J. Aust. J. Chem. 2006, 59, 340-348.
7. Burns, A. C.; Forsyth, C. J. Org. Lett. 2008, 10, 97-100.
8. Prisinzano, T. E.; Rothman, R. B. Chem. Rev. 2008, 108, 1732-1743.
9. Hasiwara. H.; Hamano. K.; Nozawa, M.; Hoshi. T.: Suzuki. T.; Kido. F. J. Org. Chem. 2005, 70, 2250-2255.
10. Cheung, A. K.; Murelli, R.; Snapper, M. L. J. Org. Chem. 2004, 69, 5712-5719.
11. Takizawa, Y.; Iwasa, Y.; Suzuki, T.; Mivaji, H. Chem. Lett. 1993, 1863-1864.
12. Carreño. C. M.: Urbano, A.; Di Vitta. C. J. Org. Chem. 1998, 63, 8320-8330.
13. Tou, J. S.: Reusch, W. J. Org. Chem. 1980, 45, 5012-5014.
14. Rainka, M. P.; Ave, Y.; Buchwald, S. L. Proc. Nat. Acad. Sci. U.S.A. 2004, 101, 5821-5823.
15. Marchand, A. P.; Reddy. M. Synthesis 1991, 198-200.
16. Comins, D. L.; Dehghani, A. Tarahedron Lett. 1992, 33, 6299-6302.
17. de Vries, J. G.; Kellog, R. M. J. Org. Chem. 1980, 45, 4126-4129.