A concise, enantioselective synthesis of (+)-decarestrictine L from Tri-O-acetyl-D-glucal

Synthesis

Volumn , Issue 14, 2010, Pages 2446-2450

  Zúñiga, Andrea ^a   Pérez, Manuel ^a   Pazos, Gonzalo ^a   Gómez, Generosa ^a   Fall, Yagamare ^a  

^a UNIVERSITY OF VIGO   (Spain)

Author keywords

Michael addition; Wacker oxidation; Wolf Kishner reaction

Indexed keywords

ENANTIOSELECTIVE SYNTHESIS; MICHAEL ADDITIONS; STEREO-SELECTIVE; WACKER OXIDATION;

ADDITION REACTIONS; OXIDATION;

SYNTHESIS (CHEMICAL);

(3 HYDROXY 6 METHYLTETRAHYDRO 2H PYRAN 2 YL)METHYL 4 METHYLBENZENESULFONATE; 1 (3 HYDROXY 6 METHYLTETRAHYDRO 2H PYRAN 2 YL)PROPAN 2 ONE; 2 (3 HYDROXY 6 METHYLTETRAHYDRO 2H PYRAN 2 YL)ACETALDEHYDE; 2 (3 HYDROXY 6 METHYLTETRAHYDRO 2H PYRAN 2 YL)ACETONITRILE; 2 (HYDROXYMETHYL) 6 METHYLTETRAHYDRO 2H PYRAN 3 OL; 2 ALLYL 6 METHYLTETRAHYDRO 2H PYRAN 3 OL; 2,2 DI TERT BUTYL 4,4A DIHYDROPYRANO[3,2 D][1,3,2]DIOXASILIN 8(8AH) ONE; 2,2 DI TERT BUTYL 4,4A,8,8A TETRAHYDROPYRANO[3,2 D][1,3,2]DIOXASILIN 8 OL; 2,2 DI TERT BUTYL 6 METHYLTETRAHYDROPYRANO[3,2 D][1,3,2]DIOXASILIN 8(8AH) ONE; 2,2 DI TERT BUTYL 6 METHYLTETRAHYDROPYRANO[3,2 D][1,3,2]DIOXASILINE; CHEMICAL COMPOUND; DECARESTRICTINE L; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; ENANTIOSELECTIVITY; MICHAEL ADDITION; OXIDATION; QUANTITATIVE STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS; SYNTHESIS; WOLFF KISHNER REDUCTION;

EID: 77954605731     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0029-1218774     Document Type: Article

References (19)

1. Grabley S, Hammann P, Huetter K, Kirsch R, Kluge H, Thiericke R, Mayer M, Zeeck A, J. Antibiot. 1992 45 1176
2. Göhrt A, Zeeck A, Hetter K, Kirsch R, Kluge H, Thiericke R, J. Antibiot. 1992 45 66
3. Mayer M, Thiericke R, J. Antibiot. 1993 46 1372
4. Machinaga N, Kibayashi C, Tetrahedron Lett. 1993 34 5739
5. Clark J S., Whitlock G A., Tetrahedron Lett. 1994 35 6381
6. Nokami J, Taniguchi T, Ogawa Y, Chem. Lett. 1995 43
7. Solladié G, Arce E, Bauder C, Carreño M C., J. Org. Chem. 1998 63 2332
8. Esumi T, Kimura R, Mori M, Iwabuchi Y, Irie H, Hatakeyama S, Heterocycles 2000 52 525
9. Lukesh J M., Donaldson W A., Tetrahedron: Asymmetry 2003 14 757
10. García I, Gómez G, Teijeira M, Terán C, Fall Y, Tetrahedron Lett. 2006 47 1333
11. Clark J S., Fessard T C., Whitlock G A., Tetrahedron 2006 62 73
12. For a recent review on biological and synthetic studies on the decarestrictine family during the last fifteen years, see:, Riatto V B., Pilli R A., Victor M M., Tetrahedron 2008 64 2279
13. Mori Y, Hayashi H, J. Org. Chem. 2001 66 8666
14. Hutchins R O., Milewski C A., Maryanoff B E., [nl] J. Am. Chem. Soc. 1973 95 3662
15. Davies M J., Moody C J., J. Chem. Soc., Perkin Trans. 1 1991 1 9
16. Marshall J A., Crooks S L., DeHoff B S., J. Org. Chem. 1988 53 1616
17. Tsuji J, Shiizu I, Yamamoto K, Tetrahedron Lett. 1976 34 2975
18. Clark J S., Fessard T C., Whitlock G A., Tetrahedron 2006 62 73
19. For our preliminary results of QSAR studies on decarestrictine L, see:, García I, Munteanu C R., Fall Y, Gómez G, Uriarte E, Gonzalez-Diaz H, Bioorg. Med. Chem. 2009 17 165