Synthesis of Enantiopure Dihydropyranones: Aldol-Based Ring Expansion of Dihydrofurans

Organic Letters

Volumn 4, Issue 18, 2002, Pages 3059-3062

  Donohoe, Timothy J ^a   Raoof, Ali ^b   Freestone, Graeme C ^a   Linney, Ian D ^c   Cowley, Andrew ^a   Helliwell, Madeleine ^b  

^a UNIVERSITY OF OXFORD   (United Kingdom)

^b UNIVERSITY OF MANCHESTER   (United Kingdom)

^c James Black Foundation   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

2 FUROIC ACID; 2-FUROIC ACID; CARBOHYDRATE; ETHER DERIVATIVE; FURAN DERIVATIVE; PYRONE DERIVATIVE;

ALKYLATION; ARTICLE; CHEMISTRY; CYCLIZATION; STEREOISOMERISM; SYNTHESIS;

ALKYLATION; CARBOHYDRATES; CYCLIZATION; ETHERS, CYCLIC; FURANS; PYRONES; STEREOISOMERISM;

EID: 0037026461     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0263595     Document Type: Article

References (19)

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6. See Landais, Y.; Zekri, E. Tetrahedron Lett. 2001, 42, 6547.
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8. See: (a) Danishefsky, S.; Cavanaugh, R. J. Am. Chem. Soc. 1968, 90, 520. (b) Danishefsky, S.; Cain P.; Nagel, A. J. Am. Chem. Soc. 1975, 97, 380. (c) Danishefsky, S.; Cain, P. J. Org. Chem. 1975, 40, 3606. (d) Kutney, J. P.; Grice, P.; Piotrowska, K.; Rettig, S. J.; Szykula, J.; Trotter, J.; Chu, L. V. Helv. Chim. Acta 1983, 66, 1820.
9. See: (a) Danishefsky, S.; Cavanaugh, R. J. Am. Chem. Soc. 1968, 90, 520. (b) Danishefsky, S.; Cain P.; Nagel, A. J. Am. Chem. Soc. 1975, 97, 380. (c) Danishefsky, S.; Cain, P. J. Org. Chem. 1975, 40, 3606. (d) Kutney, J. P.; Grice, P.; Piotrowska, K.; Rettig, S. J.; Szykula, J.; Trotter, J.; Chu, L. V. Helv. Chim. Acta 1983, 66, 1820.
10. See: (a) Danishefsky, S.; Cavanaugh, R. J. Am. Chem. Soc. 1968, 90, 520. (b) Danishefsky, S.; Cain P.; Nagel, A. J. Am. Chem. Soc. 1975, 97, 380. (c) Danishefsky, S.; Cain, P. J. Org. Chem. 1975, 40, 3606. (d) Kutney, J. P.; Grice, P.; Piotrowska, K.; Rettig, S. J.; Szykula, J.; Trotter, J.; Chu, L. V. Helv. Chim. Acta 1983, 66, 1820.
11. Donohoe, T. J.; Calabrese, A. A.; Stevenson, C. A.; Ladduwahetty, T. J. Chem. Soc., Perkin Trans. 1 2000, 3724.
12. (a) Donohoe, T. J.; Helliwell, M.; Stevenson C. A.; Ladduwahetty, T. Tetrahedron Lett. 1998, 39, 3071.
13. (b) Donohoe, T. J.; Calabrese, A. A.; Guillermin, J.-B.; Walter, D. S. Tetrahedron Lett. 2001, 42, 5841.
14. More accurate measurements on the crude mixture means that we have revised the diastereoselectivity of the reaction 7 → 8 upwards from 13:1 to 20:1; see ref 5.
15. 3) δ 1.83 (3H, s), 2.09 (6H, s), 4.50 (1H, ddd, J = 20, 3.7, and 2.1 Hz), 4.97 (1H, ddd, J = 20, 2.7, and 2.1 Hz), 6.26 (1H, ddd, J = 11, 2.7, and 2.1 Hz), 7.00-7.05 (3H, m), 7.09 (1H, ddd, J = 11, 3.7, and 2.1 Hz).
16. Greene, T. W.; Wuts, P. G. M. Protecting Groups in Organic Synthesis; Wiley: New York, 1991.
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18. Extended enolates, like pentadienyl anions, react with electrophiles at the middle carbon; see: Fleming, I. Frontier Orbitals and Organic Chemical Reactions; Wiley: Chichester, 1976.
19. Schultz, A. G.; Taveras, A. G.; Harrington, R. E. Tetrahedron Lett. 1988, 29, 3907.