Intramolecular oxonium ylide formation-[2,3] sigmatropic rearrangement of diazocarbonyl-substituted cyclic unsaturated acetals: A formal synthesis of hyperolactone C

Journal of Organic Chemistry

Volumn 79, Issue 20, 2014, Pages 9728-9734

  Hodgson, David M ^a   Man, Stanislav ^a   Powell, Kimberley J ^a   Perko, Ziga ^a   Zeng, Minxiang ^a   Moreno Clavijo, Elena ^a   Thompson, Amber L ^a   Moore, Michael D ^b  

^a UNIVERSITY OF OXFORD   (United Kingdom)

^b UNIVERSITY OF OXFORD   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL EQUATIONS; FORMAL SYNTHESIS; FULL CONTROL; HIGH SELECTIVITY; LACTONIZATION; QUATERNARY STEREOCENTERS; SIGMATROPIC REARRANGEMENTS; YLIDE FORMATION;

CATALYSIS;

1,4 BIS(TRIMETHYLSILYLOXY) 2 METHYLBUT 2 ENE; 1,4 BIS(TRIMETHYLSILYLOXY) 2,3 DIMETHYLBUT 2 ENE; 2 [ 9 METHYL 4,6 DIOXO 2 PHENYL 1,7 DIOXASPIRO (4.4)NON 2 EN 9YL]ACRYLALDEHYDE; 9 ACETYL 9 METHYL 1,7 DIOXASPIRO[4.4]NON 2 ENE 4,6 DIONE; 9 METHYL 2 PHENYL 9 (PROP 1 EN 2 YL) 1,7 DIOXASPIRO[4.4]NON 2 ENE 4,6 DIONE; 9 METHYL 9 (PROP 1 EN 2 YL) 1,7 DIOXASPIRO[4.4]NON 2 ENE 4,6 DIONE; 9 METHYL 9 VINYL 1,7 DIOXASPIRO[4.4]NON 2 ENE 4,6 DIONE; 9 VINYL 1,7 DIOXASPIRO[4.4]NON 2 ENE 4,6 DIONE; ACETAL DERIVATIVE; CARBONYL DERIVATIVE; HYPEROLACTONE C; LACTONE DERIVATIVE; METHYL 2 DIAZO 4 (2 PHENYL 4,7 DIHYDRO 1,3 DIOXEPIN 2 YL) 3 OXOBUTANOATE; METHYL 2 DIAZO 4 (4,7 DIHYDRO 1,3 DIOXEPIN 2 YL) 3 OXOBUTANOATE; METHYL 2 DIAZO 4 (5 METHYL 4,7 DIHYDRO 1,3 DIOXEPIN 2 YL) 3 OXOBUTANOATE; METHYL 2 DIAZO 4 (5,6 DIMETHYL 2 PHENYL 4,7 DIHYDRO 1,3 DIOXEPIN 2 YL) 3 OXOBUTANOATE; METHYL 2 DIAZO 4 (5,6 DIMETHYL 4,7 DIHYDRO 1,3 DIOXEPIN 2 YL) 3 OXOBUTANOATE; METHYL 2 DIAZO 5,5 DIETHOXY 3 OXOPENTANOATE; METHYL 4 (2 PHENYL 4,7 DIHYDRO 1,3 DIOXEPIN 2 YL) 3 OXOBUTANOATE; METHYL 4 (5,6 DIMETHYL 2 PHENYL 4,7 DIHYDRO 1,3 DIOXEPIN 2 YL) 3 OXOBUTANOATE; METHYL 4 METHYL 6 OXO 1 PHENYL 4 (PROP 1 EN 2 YL) 2,8 DIOXABICYCLO[3.2.1]OCTANE 5 CARBOXYLATE; METHYL 4 METHYL 6 OXO 4 (3 OXOPROP 1 EN 2 YL) 2,8 DIOXABICYCLO[3.2.1]OCTANE 5 CARBOXYLATE; METHYL 4 METHYL 6 OXO 4 (PROP 1 EN 2 YL) 2,8 DIOXABICYCLO[3.2.1]OCTANE 5 CARBOXYLATE; METHYL 4 METHYL 6 OXO 4 VINYL 2,8 DIOXABICYCLO[3.2.1]OCTANE 5 CARBOXYLATE; METHYL 5,5 DIMETHOXY 3 OXO 5 PHENYLPENTANOATE; METHYL 6 OXO 4 VINYL 2,8 DIOXABICYCLO[3.2.1]OCTANE 5 CARBOXYLATE; UNCLASSIFIED DRUG; ZIDOVUDINE; CATION; FURAN DERIVATIVE; HYDRONIUM ION; RHODIUM; SPIRO COMPOUND;

ARTICLE; CONTROLLED STUDY; DRUG POTENCY; DRUG SELECTIVITY; DRUG SYNTHESIS; IC50; LACTONIZATION; STEREOCHEMISTRY; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ACETALS; FURANS; MOLECULAR STRUCTURE; ONIUM COMPOUNDS; RHODIUM; SPIRO COMPOUNDS; STEREOISOMERISM;

EID: 84907997445     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo501893r     Document Type: Article

References (26)

1. Aramaki, Y.; Chiba, K.; Tada, M. Phytochemistry 1995, 38, 1419-1421.
2. Nicolaou, K. C.; Wu, T. R.; Sarlah, D.; Shaw, D. M.; Rowcliffe, E.; Burton, D. R. J. Am. Chem. Soc. 2008, 130, 11114-11121.
3. Nicolaou, K. C.; Sanchini, S.; Sarlah, D.; Lu, G.; Wu, T. R.; Nomura, D. K.; Cravatt, B. F.; Cubitt, B.; de la Torre, J. C.; Hessell, A. J.; Burton, D. R. Proc. Natl. Acad. Sci. U.S.A. 2011, 108, 6715-6720.
4. Hodgson, D. M.; Angrish, D.; Erickson, S. P.; Kloesges, J.; Lee, C. H. Org. Lett. 2008, 10, 5553-5556.
5. Hodgson, D. M.; Man, S. Chem. - Eur. J. 2011, 17, 9731-9737.
6. Hodgson, D. M.; Moreno-Clavijo, E.; Day, S. E.; Man, S. Org. Biomol. Chem. 2013, 11, 5362-5369.
7. Murphy, G. K.; Stewart, C.; West, F. G. Tetrahedron 2013, 69, 2667-2686.
8. Wu, Y.; Du, C.; Hu, C.; Li, Y.; Xie, Z. J. Org. Chem. 2011, 76, 4075-4081.
9. Calter, M. A.; Sugathapala, P. M. Tetrahedron Lett. 1998, 39, 8813-8816.
10. Bagley, M. C.; Buck, R. T.; Hind, S. L.; Moody, C. J. J. Chem. Soc., Perkin Trans. 1 1998, 591-600.
11. Downey, C. W.; Johnson, M. W.; Tracy, K. J. J. Org. Chem. 2008, 73, 3299-3302.
12. See the Supporting Information for details.
13. (a) Akgün, E.; Pindur, U. Liebigs Ann. Chem. 1985, 2472-2476.
14. (b) Liu, Y.; Liu, Y.; Shanahan, C. S.; Xu, X.; Doyle, M. P. Org. Biomol. Chem. 2014, 12, 5227-5234.
15. Moody, C. J.; Miah, S.; Slawin, A. M. Z.; Mansfield, D. J.; Richards, I. C. J. Chem. Soc., Perkin Trans. 1 1998, 4067-4075.
16. Tsuji, J.; Ohno, K. Tetrahedron Lett. 1965, 6, 3969-3971.
17. Kreis, M.; Palmelund, A.; Bunch, L.; Madsen, R. Adv. Synth. Catal. 2006, 348, 2148-2154.
18. Iwai, T.; Fujihara, T.; Tsuji, Y. Chem. Commun. 2008, 6215-6217.
19. Doyle, M. P.; Bagheri, V.; Harn, N. K. Tetrahedron Lett. 1988, 29, 5119-5122.
20. Shimada, N.; Nakamura, S.; Anada, M.; Shiro, M.; Hashimoto, S. Chem. Lett. 2009, 38, 488-489.
21. Hodgson, D. M.; Pierard, F. Y. T. M.; Stupple, P. A. Chem. Soc. Rev. 2001, 30, 50-61.
22. Kim, J. H.; Čorić, I.; Vellalath, S.; List, B. Angew. Chem., Int. Ed. 2013, 52, 4474-4477.
23. See the Supporting Information for general experimental conditions.
24. Hwu, J. R.; Anderson, D. A.; Wang, N.; Buchner, M. M.; Gani, P.; Tsay, S.-C. Chem. Ber. 1990, 123, 1667-1671.
25. Müller, P.; Rodriguez, D. Helv. Chim. Acta 1985, 68, 975-980.
26. Ren, R. X-F.; Nakanishi, K. Aldrichimica Acta 1997, 30, 106.