Transannular Diels-Alder model studies on the total synthesis of chatancin. The furanophane approach. Part 1: Assembly of the acyclic substrates

Tetrahedron Letters

Volumn 40, Issue 14, 1999, Pages 2765-2768

  Toró, András ^a   Wang, Yuan ^a   Deslongchamps, Pierre ^a  

^a UNIVERSITÉ DE SHERBROOKE   (Canada)

Author keywords

Dithianes; Furans; Lithiations; Macrocycles

Indexed keywords

CHATANCIN; FUNCTIONAL GROUP; FURAN DERIVATIVE; FURANOPHANE; FURFURAL; MACROCYCLIC COMPOUND; MALONIC ACID DERIVATIVE; THROMBOCYTE ACTIVATING FACTOR ANTAGONIST; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION; CONFORMATION; CONFORMATIONAL TRANSITION; CYCLIZATION; MOLECULAR MODEL; REACTION ANALYSIS; SYNTHESIS;

EID: 0033515731     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00323-8     Document Type: Article

References (25)

1. For a recent review on furan Diels-Alder chemistry see: Kappe CO, Murphree SS, Padwa A. Tetrahedron 1997;53:14179-14233.
2. Marshall JA, Wang X-J. J. Org. Chem. 1992;57:3387-3396.
3. Cattalini M, Cossu S, Fabris F, De Lucchi O. Synth. Comm. 1996;26:637-647.
4. Deslongchamps P. Pure Appl. Chem. 1992;64:1831-1847.
5. Sugano M, Shindo T, Sato A, Iijima Y, Oshima T, Kuwano H, Hata T. J. Org. Chem. 1990;55:5803-5805.
6. Rodriguez AD. Tetrahedron 1995;51:4571-4618. Coll JC. Chem. Rev. 1992;92:613-631.
7. Rodriguez AD. Tetrahedron 1995;51:4571-4618. Coll JC. Chem. Rev. 1992;92:613-631.
8. For a recent total synthesis of chatancin see: Aigner J, Gössinger E, Kählig H, Menz T, Pflugseder K. Angew. Chem. Int. Ed. 1998;37:2226-2228.
9. See subsequent communication: Toró A, Wang Y, Drouin M, Deslongchamps P. Tetrahedron Letters 1999;40:2769-2772.
10. 13C NMR, IR as well as mass spectra were in full agreement with the synthesized structures depicted.
11. Abbreviations used in this communication: Bn: benzyl, BuLi: butyllithium. Bz: benzoate, DIBALH: diisobutylaluminumhydride, DMF: dimethylformamide, DMSO: dimethylsulfoxide, E: COOMe, HCA: hexachloroacetone, MOM: methoxymethyl, Ms: mesyl, NMO: N-methylmorpholine N-oxide, PAF: platelet activating factor, Piv: pivalate. Py: pyridine, PTSA: paratoluenesulfonic acid, TBAF: tetrabutylammonium fluoride, TBDMS: tert-butyldimethylsilyl, TBDPS: tert-butyldiphenylsilyl. Tf: triflate, THP: tetrahydropyranyl, TPAP: tetrapropylammonium perrhuthenate.
12. Mancuso AJ, Swern D. Synthesis, 1981;165-185.
13. McDougal PG, Rico JG, Oh Y-I, Condon BD. J. Org. Chem. 1986;51:3388-3390.
14. Johnson WS, Werthemann L, Bartlett Wr, Brocksom TJ, Li T, Faulkner DJ, Petersen MR. J. Am. Chem. Soc. 1970;92:741-743.
15. Unprotected 10 is commercial, for synthesis of 11 see: Toró A, Deslongchamps P. Synth. Comm. 1998;28(23):0000. Accepted for publication.
16. Sternbach DD, Rossana DM. Tetrahedron Let. 1982;23:303-306
17. Hall DG, Caillé A-S, Drouin M, Lamothe S, Müller R, Deslongchamps P. Synthesis, 1995;54:1081-1088.
18. Collington EW, Meyers AI. J. Org. Chem. 1971;36:3044-3045.
19. Magid RM, Talley BG, Souther SK. J. Org. Chem. 1981;46:824-825.
20. Leopold EJ. Org. Synth. 1986;64:164-173.
21. Cartaya-Marin CP, JACkson AC, Snider BB. J. Org.chem. 1984;49:2443-2446.
22. Birch AJ, Walker KAM. Aust. J. Chem. 1971;24:513-520.
23. Ley SV, Norman J, Griffith WP, Marshden SP. Synthesis, 1994;639-666.
24. Knight DW, Nott AP. J. Chem. Soc. Perkin I. 1981;1125-1131.
25. Fr. 1,578,377 patent to Sumitomo Chemical Co., Ltd. (C.A. 1970;72:121350j.)