Thieme chemistry journal awardees - Where are they now? Approaches to tagetitoxin and its decarboxy analogue from d -glucose

Synlett

Volumn , Issue 20, 2009, Pages 3258-3262

  Plet, Julien R H ^a   Sandhu, Amandeep Kaur ^a   Sehailia, Moussa ^a   Porter, Michael J ^a  

^a UNIVERSITY COLLEGE LONDON   (United Kingdom)

Author keywords

Alkynes; Carbohydrates; Natural products; Organometallic reagents; Stereoselective synthesis

Indexed keywords

ALKYNE DERIVATIVE; BACTERIAL TOXIN; CARBOHYDRATE; ENZYME INHIBITOR; GLUCOSE; GLYCOSIDE; TAGETITOXIN; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; DRUG SYNTHESIS; ESTERIFICATION; HYDROLYSIS; OXIDATION; PRECURSOR; REDUCTION; STEREOCHEMISTRY;

EID: 72249104705     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0029-1218525     Document Type: Article

References (29)

1. Mitchell R E., Durbin R D., Physiol. Plant Pathol. 1981 18 157
2. Mathews D E., Durbin R D., J. Biol. Chem. 1990 265 493
3. Steinberg T H., Mathews D E., Durbin R D., Burgess R R., J. Biol. Chem. 1990 265 499
4. Mitchell R E., Coddington J M., Young H, Tetrahedron Lett. 1989 30 501
5. Gronwald J W., Plaisance K L., Marimanikkuppam S, Ostrowski B G., Physiol. Mol. Plant Pathol. 2005 67 23
6. Sammakia T, Hurley T B., Sammond D M., Smith R S., Sobolov S B., Oeschger T R., Tetrahedron Lett. 1996 37 4427
7. Dent B R., Furneaux R H., Gainsford G J., Lynch G P., Tetrahedron 1999 55 6977
8. Plet J R. H., Porter M J., Chem. Commun. 2006 1197
9. Mortimer A J. P., Aliev A E., Tocher D A., Porter M J., Org. Lett. 2008 10 5477
10. Mehta S, Jordan K L., Weimar T, Kreis U C., Batchelor R J., Einstein F W. B., Pinto B M., Tetrahedron: Asymmetry 1994 5 2367
11. Harvey J E., Raw S A., Taylor R J. K., Org. Lett. 2004 6 2611
12. Pasetto P, Franck R W., J. Org. Chem. 2003 68 8042
13. Dess D B., Martin J C., J. Org. Chem. 1983 48 4155
14. Ireland R E., Liu L, J. Org. Chem. 1993 58 2899
15. -1. 1H NMR (500 MHz, CDCl3): d = 7.48×7.43 (3 H, m), 7.36×7.28 (2 H, m), 5.49 (1 H, s), 4.35 (1 H, dd, J = 2.9, 0.9 Hz), 4.21 (1 H, d, J = 2.9 Hz), 4.33 (1 H, dd, J = 11.0, 5.8 Hz), 4.09 (1 H, dddd, J = 10.2, 8.9, 5.8, 2.9 Hz), 3.83 (1 H, dd, J = 9.9, 0.9 Hz), 3.74 (1 H, dd, J = 8.9, 2.9 Hz), 3.63 (1 H, dd, J = 11.0, 10.2 Hz), 3.28 (1 H, d, J = 9.9 Hz), 0.90 (9 H, s), 0.28 (3 H, s), 0.27 (3 H, s), 0.18 (18 H, s). 13C NMR (125 MHz, CDCl3): d = 137.4 (C), 129.0 (CH), 128.3 (CH), 126.1 (CH), 103.1 (C), 102.1 (C), 100.1 (CH), 91.6 (C), 91.5 (C), 84.4 (CH), 75.9 (CH), 70.1 (CH2), 67.1 (C), 63.8 (CH), 60.7 (CH), 25.5 (CH3), 18.7 (C), -0.5 (CH3), -0.6 (CH3), -3.5 (CH3), -3.6 (CH3). HRMS-FAB+: m/z calcd for C29H47O5N3Si3Na [MNa+]: 624.2721; found: 624.2735. 4-Azido-1,3-O-benzylidene-5-O-tert-butyldimethylsilanyl- 4,7,8-trideoxy-8-trimethylsilanyl-b-L-manno-oct- 7-yn-2-ulopyranose (12) [a]D 20 -105.5 (c 0.4, CH2Cl2). IR (CHCl3 cast): nmax = 3445, 3053, 2304, 1633, 1421 cm-1. 1H NMR (500 MHz, CDCl3): d = 7.47×7.42 (2 H, m), 7.33×7.24 (3 H, m), 5.56 (1 H, s), 4.76 (1 H, d, J = 6.2 Hz), 4.32 (1 H, dd, J = 10.3, 6.2 Hz), 4.23 (1 H, d, J = 2.8 Hz), 4.07 (1 H, dd, J = 10.3, 2.8 Hz), 4.03 (1 H, d, J = 11.9 Hz), 3.74 (1 H, s), 3.69 (1 H, d, J = 11.9 Hz), 0.91 (9 H, s), 0.17 (9 H, s), 0.13 (3 H, s), 0.11 (3 H, s). 13C NMR (125 MHz, CDCl3): d = 136.7 (C), 129.0 (CH), 128.2 (CH), 126.0 (CH), 103.0 (C), 100.8 (CH), 95.0 (C), 91.9 (C), 78.9 (CH), 73.5 (CH2), 67.6 (CH), 66.3 (CH), 58.8 (CH), 25.5 (CH3), 17.8 (C), -0.5 (CH3), -4.7 (CH3), -5.0 (CH3). HRMS-FAB+: m/z calcd for C24H37O5N3Si2Na [MNa+]: 26.2169; found: 526.2158. 1-[2-O-Acetyl-6-S-acetyl-3-azido-3-deoxy-6- thio-4-O- (triethylsilanyl)-b-D-altropyranosyl]-2-bromoethyne (23) [a]D 18 +5.1 (c 0.3, CHCl3). IR (CHCl3 cast): nmax = 2947, 2110, 1755, 1693 cm-1. 1H NMR (500 MHz, CDCl3): d = 4.94 (1 H, dd, J = 3.1, 1.5 Hz), 4.52 (1 H, d, J = 1.4 Hz), 3.87×3.83 (2 H, m), 3.71 (1 H, td, J = 9.2, 2.6 Hz), 3.60 (1 H, dd, J = 13.6, 2.7 Hz), 2.74 (1 H, dd, J = 13.6, 9.5 Hz), 2.33 (3 H, s), 2.16 (3 H, s), 0.99 (9 H, t, J = 8.0 Hz), 0.68×0.62 (6 H, m). 13C NMR (125 MHz, CDCl3): d = 195.0 (C), 169.7 (C), 76.0 (CH), 74.2 (C), 71.5 (CH), 70.0 (CH), 65.9 (CH), 61.6 (CH), 47.8 (C), 31.2 (CH2), 30.5 (CH3), 20.7 (CH3), 6.7 (CH3), 4.8 (CH2). HRMS-FAB+: m/z calcd for C18H29O5N3SSi79Br [MH+]: 506.0781; found: 506.0771. 1-(2,4-Di-O-triethylsilanyl-5-C-vinyl-b-D-glucopyranosyl)- 2- imethylsilanylethyne (28) [a]D 22 -65.9 (c 0.7, CHCl3). IR (CHCl3 cast): nmax = 3565, 2182, 1729, 1458 cm-1. 1H NMR (600 MHz, CDCl3): d = 6.00 (1 H, dd, J = 18.0, 11.3 Hz), 5.45 (1 H, dd, J = 18.1, 1.4 Hz), 5.43 (1 H, dd, J = 11.2, 1.2 Hz), 4.21 (1 H, d, J = 9.5 Hz), 3.83 (1 H, d, J = 9.8 Hz), 3.56 (1 H, dd, J = 11.7, 11.0 Hz), 3.48 (1 H, dd, J = 9.5, 8.8 Hz), 3.39 (1 H, dd, J = 11.9, 2.9 Hz), 3.36 (1 H, ddd, J = 9.5, 8.9, 3.0 Hz), 2.19 (1 H, dd, J = 10.9, 3.1 Hz), 2.09 (1 H, d, J = 2.9 Hz), 0.99 (18 H, m), 0.71 (12 H, m), 0.20 (9 H, s). 13C NMR (150 MHz, CDCl3): d = 132.5 (CH), 119.2 (CH2), 103.4 (C), 89.9 (C), 81.7 (C), 76.0 (CH), 75.9 (CH), 71.0 (CH), 66.7 (CH), 65.9 (CH2), 6.9 (CH3), 5.2 (CH2), 5.3 (CH2), 5.1 (CH2), -0.2 (CH3). HRMS (CI+): m/z calcd for C25H50O5Si3 [MH+]: 515.3044; found:515.3050.
16. Burkhardt E R., Molander G A., Weinig P, J. Org. Chem. 1990 55 4990
17. Boons G.-J, Isles S, Setälä P, Synlett 1995 755
18. Ernst A, Schweizer W B., Vasella A, Helv. Chim. Acta 1998 81 2157
19. Steglich W, Höfle G, Angew. Chem., Int. Ed. Engl. 1969 8 981
20. Vedejs E, Diver S T., J. Am. Chem. Soc. 1993 115 3358
21. Steglich W, Höfle G, Tetrahedron Lett. 1970 4727
22. Hassner A, Krepski L R., Alexanian V, Tetrahedron 1978 34 2069
23. Smith A B. III., Rivero R A., J. Am. Chem. Soc. 1987 109 1272
24. Meguro M, Asao N, Yamamoto Y, J. Chem. Soc., Chem. Commun. 1995 1021
25. Hofmeister H, Annen K, Laurent H, Wiechert R, Angew. Chem., Int. Ed. Engl. 1984 23 727
26. Yamamoto Y, Chem. Rev. 2008 108 3199
27. Li L S., Wu Y L., Tetrahedron Lett. 2002 43 2427
28. Rao A V. R., Gurjar M K., Devi T R., Kumar K R., Tetrahedron Lett. 1993 34 1653
29. 1,6-Anhydro-5-C-vinyl-b-D-glucopyranose (27) Thioanisole (0.17 mL, 2.1 mmol) was added to a stirred solution of glucofuranoside 26 (1.00 g, 2.08 mmol) and TFA (0.05 mL, 0.4 mmol) in 80% aq AcOH (20.8 mL). The mixture was stirred under reflux for 3 d, concentrated in vacuo, and co-evaporated with heptane (3 ×80 mL) to give a viscous black oil. MeOH (40 mL) was added and the organic solution removed from the insoluble residue using a Pasteur pipette. NaOMe (225 mg, 4.16 mmol) was added to the MeOH solution and the mixture stirred for 3 h. The solution was concentrated in vacuo and the residue purified by flash column chromatography (MeOH-CH2Cl2 1:99 10:90) to give compound 27 (284 mg, 73%) as a viscous brown oil; [a]D 20 -73.1 (c 1.0, EtOH). IR (neat): nmax = 3368, 2901, 1646, 1416 cm-1. 1H NMR (600 MHz, CD3OD): d = 6.05 (1 H, dd, J = 17.6, 11.2 Hz), 5.44 (1 H, dd, J = 17.6, 1.3 Hz), 5.44 (1 H, br t, J = 1.6 Hz), 5.31 (1 H, dd, J = 11.2, 1.3 Hz), 4.32 (1 H, d, J = 7.0 Hz), 3.82 (1 H, br q, J = 1.5 Hz), 3.59 (1 H, br s), 3.45 (1 H, br q, J = 1.5 Hz), 3.42 (1 H, d, J = 7.0 Hz). 13C NMR (150 MHz, CD3OD): d = 135.0 (CH), 115.1 (CH2), 103.1 (CH), 82.6 (C), 74.1 (CH), 72.6 (CH), 69.6 (CH), 69.4 (CH2). HRMS (CI+): m/z calcd for C8H13O5 [MH+]: 189.0763; found: 189.0765.