Transannular Diels-Alder model studies on the total synthesis of chatancin. The furanophane approach. Part 2 [1]: Macrocyclization and Diels- Alder reaction

Tetrahedron Letters

Volumn 40, Issue 14, 1999, Pages 2769-2772

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

^a UNIVERSITÉ DE SHERBROOKE   (Canada)

Author keywords

Diels Alder reactions; Furans; Macrocycles; Transannular reactions

Indexed keywords

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

ARTICLE; CATALYSIS; CHEMICAL REACTION; CYCLIZATION; MOLECULAR MODEL; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS; THERMOSTABILITY;

EID: 0033515732     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00324-X     Document Type: Article

References (16)

1. For Part 1, see preceding communication: Toró A. Wang Y, Deslongchamps P. Tetrahedron Letters 1999;40: 2765-2768.
2. Sugano M, Shindo T, Sato A, Iijima Y, Oshima T, Kuwano H, Hata T. J. Org. Chem. 1990;55:5803-5805.
3. 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.
4. Deslongchamps P. Pure Appl. Chem. 1992;64:1831-1847.
5. Marshall JA, Wang X-J. J. Org. Chem. 1992;57:3387-3396.
6. Cattalini M, Cossu S, Fabris F, De Lucchi O. Synth. Comm. 1996;26:637-647.
7. For abbreviations see Part 1: ref. 1, note 7.
8. Depicted structures represent only relative stereochemistry.
9. 13C NMR, IR as well as mass spectra. Structure 7, 10, 11, 13, 17, 18 and 19 were also verified by X-ray crystallography (deposited to Cambridge Cristallographic Data Center).
10. - (Bauld N. Tetrahedron 1989;45:5307-5363) at 0°C, a quantitative isomerization to 11 was observed.
11. 11 resisted thermic TADA reaction: it was intact after a week at 80°C and it underwent only slow decomposition at 190°C.
12. 1 diastereoisomers (note 7) are depicted and syn-anti symbols denote the relative stereochemistry of the bridge and the adjacent oxygen functionality.) (formula presented)
13. A geminal dialkyl- dialkoxy- or dithioalkyl-group is considered advantageous in the intramolecular Diels-Alder reactions, for further information see: Parrill AL, Dolata DP. Tetrahedron Letters 1994;35:7319-7322 and references cited therein.
14. Jung ME, Gervay J. J. Am. Chem. Soc. 1989;111:5469-5470 and references cited therein.
15. Yu S, Beese G, Keay BA. J. Chem. Soc. Perkin Trans. 1, 1992;2729-2731.
16. So far, we could not induce the oxygen transposition on 17: with Lewis acid treatment only slow decomposition was observed.