Formation of stable spiro[4.4] ortho ester aminals during the synthesis of the C26-C32 oxazole fragment of calyculin C

Journal of Organic Chemistry

Volumn 64, Issue 2, 1999, Pages 652-654

  Pihko, Petri M ^a   Koskinen, Ari M P ^a   Nissinen, Maija J ^b   Rissanen, Kari ^b  

^a UNIVERSITY OF OULU   (Finland)

^b UNIVERSITY OF JYVÄSKYLÄ   (Finland)

Author keywords

[No Author keywords available]

Indexed keywords

ESTER; HETEROCYCLIC AMINE; OXAZOLE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; ISOMER; OXIDATION; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 0033593279     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo981674j     Document Type: Article

References (27)

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2. For examples, see: (a) Feinauer, R. Angew. Chem. 1966, 78, 938. (b) Doleschall, G.; Lempert, K. Tetrahedron 1968, 24, 5529-5545. (c) Fryer, R. I.; Earley, J. V.; Blount, J. F. J. Org. Chem. 1977, 42, 2212- 2219. (d) Gotthardt, H.; Schenk, K.-H. Angew. Chem. 1985, 97, 604- 606. (e) Knölker, H.-J.; Boese, R.; Döring, D.; El-Ahl, A.-A.; Hitzemann, R.; Jones, P. G. Chem. Ber. 1992, 125, 1939-1951. (e) Kappe, C. O.; Peters, K.; Peters, E.-M. J. Org. Chem. 1997, 62, 3109-3118. (f) Couture, P.; Warkentin, J. Can. J. Chem. 1997, 75, 1264-1280,1281- 1294.
3. For examples, see: (a) Feinauer, R. Angew. Chem. 1966, 78, 938. (b) Doleschall, G.; Lempert, K. Tetrahedron 1968, 24, 5529-5545. (c) Fryer, R. I.; Earley, J. V.; Blount, J. F. J. Org. Chem. 1977, 42, 2212-2219. (d) Gotthardt, H.; Schenk, K.-H. Angew. Chem. 1985, 97, 604- 606. (e) Knölker, H.-J.; Boese, R.; Döring, D.; El-Ahl, A.-A.; Hitzemann, R.; Jones, P. G. Chem. Ber. 1992, 125, 1939-1951. (e) Kappe, C. O.; Peters, K.; Peters, E.-M. J. Org. Chem. 1997, 62, 3109-3118. (f) Couture, P.; Warkentin, J. Can. J. Chem. 1997, 75, 1264-1280,1281- 1294.
4. For examples, see: (a) Feinauer, R. Angew. Chem. 1966, 78, 938. (b) Doleschall, G.; Lempert, K. Tetrahedron 1968, 24, 5529-5545. (c) Fryer, R. I.; Earley, J. V.; Blount, J. F. J. Org. Chem. 1977, 42, 2212- 2219. (d) Gotthardt, H.; Schenk, K.-H. Angew. Chem. 1985, 97, 604-606. (e) Knölker, H.-J.; Boese, R.; Döring, D.; El-Ahl, A.-A.; Hitzemann, R.; Jones, P. G. Chem. Ber. 1992, 125, 1939-1951. (e) Kappe, C. O.; Peters, K.; Peters, E.-M. J. Org. Chem. 1997, 62, 3109-3118. (f) Couture, P.; Warkentin, J. Can. J. Chem. 1997, 75, 1264-1280,1281- 1294.
5. For examples, see: (a) Feinauer, R. Angew. Chem. 1966, 78, 938. (b) Doleschall, G.; Lempert, K. Tetrahedron 1968, 24, 5529-5545. (c) Fryer, R. I.; Earley, J. V.; Blount, J. F. J. Org. Chem. 1977, 42, 2212- 2219. (d) Gotthardt, H.; Schenk, K.-H. Angew. Chem. 1985, 97, 604- 606. (e) Knölker, H.-J.; Boese, R.; Döring, D.; El-Ahl, A.-A.; Hitzemann, R.; Jones, P. G. Chem. Ber. 1992, 125, 1939-1951. (e) Kappe, C. O.; Peters, K.; Peters, E.-M. J. Org. Chem. 1997, 62, 3109-3118. (f) Couture, P.; Warkentin, J. Can. J. Chem. 1997, 75, 1264-1280,1281- 1294.
6. For examples, see: (a) Feinauer, R. Angew. Chem. 1966, 78, 938. (b) Doleschall, G.; Lempert, K. Tetrahedron 1968, 24, 5529-5545. (c) Fryer, R. I.; Earley, J. V.; Blount, J. F. J. Org. Chem. 1977, 42, 2212- 2219. (d) Gotthardt, H.; Schenk, K.-H. Angew. Chem. 1985, 97, 604- 606. (e) Knölker, H.-J.; Boese, R.; Döring, D.; El-Ahl, A.-A.; Hitzemann, R.; Jones, P. G. Chem. Ber. 1992, 125, 1939-1951. (e) Kappe, C. O.; Peters, K.; Peters, E.-M. J. Org. Chem. 1997, 62, 3109-3118. (f) Couture, P.; Warkentin, J. Can. J. Chem. 1997, 75, 1264-1280,1281- 1294.
7. For examples, see: (a) Feinauer, R. Angew. Chem. 1966, 78, 938. (b) Doleschall, G.; Lempert, K. Tetrahedron 1968, 24, 5529-5545. (c) Fryer, R. I.; Earley, J. V.; Blount, J. F. J. Org. Chem. 1977, 42, 2212- 2219. (d) Gotthardt, H.; Schenk, K.-H. Angew. Chem. 1985, 97, 604- 606. (e) Knölker, H.-J.; Boese, R.; Döring, D.; El-Ahl, A.-A.; Hitzemann, R.; Jones, P. G. Chem. Ber. 1992, 125, 1939-1951. (e) Kappe, C. O.; Peters, K.; Peters, E.-M. J. Org. Chem. 1997, 62, 3109-3118. (f) Couture, P.; Warkentin, J. Can. J. Chem. 1997, 75, 1264-1280,1281-1294.
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11. For a review of ortho esters, see: DeWolfe, R. H. Synthesis 1974, 153-172. For recent use of ortho esters in synthesis, see: Charette, A. B.; Chua, P. Tetrahedron Lett. 1997, 38, 8499-8502 and references therein.
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16. 13C NMR. We are grateful to an anynomous reviewer for drawing our attention to this point.
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18. (b) Method B: see ref 8.
19. 2) is presented in ref 10a. These transfers are not necessarily synchronous.
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21. See the Supporting Information for the X-ray data. There are two crystallographically independent molecules in the unit cell, which have essentially identical geometries and bond lengths. In the text, only the dimensions of the molecule A are discussed.
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