Solid-phase synthesis of hydroxy-acids leading to macrolactones

Tetrahedron Letters

Volumn 41, Issue 24, 2000, Pages 4751-4755

  Gagnon, René ^a   Dory, Yves L ^a   Deslongchamps, Pierre ^a  

^a UNIVERSITÉ DE SHERBROOKE   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ARTICLE; CHEMICAL STRUCTURE; CYCLIZATION; ESTERIFICATION; SOLID PHASE EXTRACTION; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0034660540     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00711-5     Document Type: Article

References (13)

1. Ramaseshan, M.; Ellingboe, J. W.; Dory, Y. L.; Deslongchamps, P. Tetrahedron Lett., in press.
2. Crowley, J. I.; Rapoport, H. J. Am. Chem. Soc. 1970, 92, 6363.
3. Norcross, R. D.; Paterson, I. Chem. Rev. 1995, 95, 2041.
4. Deslongchamps, P. Aldrichimica Acta 1991, 24, 43; Pure Appl. Chem. 1992, 64, 1831.
5. Deslongchamps, P. Aldrichimica Acta 1991, 24, 43; Pure Appl. Chem. 1992, 64, 1831.
6. Deslongchamps, P.; Lamothe, S.; Lin, H.-S. Can. J. Chem. 1987, 65, 56.
7. Mitsunobu, O. Synthesis 1981, 1.
8. 6-Aminohexan-1-ol was treated with TsCl and 2N NaOH in ethyl acetate and water to yield the corresponding tosylamide (85%) whose alcohol was protected as a THP ether (PTSA and DHP) to give 7 in 68% yield. Compound 8 was obtained in the same manner from 6-Aminohexan-1-ol and NsCl with a yield of 54% for the two reactions.
9. Yang, L.; Chiu, K. Tetrahedron Lett. 1997, 38, 7307.
10. +.
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12. +: 571.2240; found: 571.2233.
13. +: 602.1934; found: 602.1939.