"Endo" and "Exo" Bicyclo[4.2.0]-octadiene Isomers from the Electrocyclization of Fully Substituted Tetraene Models for SNF 4435C and D. Control of Stereochemistry by Choice of a Functionalized Substituent

Organic Letters

Volumn 6, Issue 2, 2004, Pages 161-164

  Parker, Kathlyn A ^a   Lim, Yeon Hee ^a  

^a STONY BROOK UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; BICYCLO COMPOUND; BICYCLO[4.2.0]OCTADIENE DERIVATIVE; IMMUNOSUPPRESSIVE AGENT; SNF 4435 C; SNF 4435 D; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; DRUG SYNTHESIS; ELECTROCYCLIZATION; ISOMER; METHODOLOGY; MODEL; STEREOCHEMISTRY;

CYCLIZATION; ELECTRONS; ISOMERISM; MOLECULAR CONFORMATION; NITRO COMPOUNDS; PYRONES; STEREOISOMERISM;

EID: 0842306919     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol036048+     Document Type: Article

References (18)

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12. Although 8π, 6π closures of 1,8-disubstituted 1,3,5,7-(E,Z,Z,E)- tetraenes proceed at low temperature (e.g., 2,4,6,8-(E,Z,Z,E)-decatetraene closes at -10°C over 30 h and the subsequent electrocylization occurs at 20°C over 8 h), closure of (Z,Z,Z,E)-tetraenes requires higher temperatures (9°C for the first step and 40°C for the second step) and the closure of Z,Z,Z,Z-substrates is even slower, affording the [4.2.0] product directly at 65°C. See: (a) Huisgen, R.; Dahmen, A.; Huber, H. J. Am. Chem. Soc. 1967, 89, 7130. (b) Huisgen, R.; Dahmen, A.; Huber, H. Tetrahedron Lett. 1969, 1461. (c) For a related example and a literature survey, see: Hayashi, R.; Fernandez, S.; Okamura, W. H. Org. Lett. 2002, 4, 851.
13. Although 8π, 6π closures of 1,8-disubstituted 1,3,5,7-(E,Z,Z,E)- tetraenes proceed at low temperature (e.g., 2,4,6,8-(E,Z,Z,E)-decatetraene closes at -10°C over 30 h and the subsequent electrocylization occurs at 20°C over 8 h), closure of (Z,Z,Z,E)-tetraenes requires higher temperatures (9°C for the first step and 40°C for the second step) and the closure of Z,Z,Z,Z-substrates is even slower, affording the [4.2.0] product directly at 65°C. See: (a) Huisgen, R.; Dahmen, A.; Huber, H. J. Am. Chem. Soc. 1967, 89, 7130. (b) Huisgen, R.; Dahmen, A.; Huber, H. Tetrahedron Lett. 1969, 1461. (c) For a related example and a literature survey, see: Hayashi, R.; Fernandez, S.; Okamura, W. H. Org. Lett. 2002, 4, 851.
14. Although 8π, 6π closures of 1,8-disubstituted 1,3,5,7-(E,Z,Z,E)- tetraenes proceed at low temperature (e.g., 2,4,6,8-(E,Z,Z,E)-decatetraene closes at -10°C over 30 h and the subsequent electrocylization occurs at 20°C over 8 h), closure of (Z,Z,Z,E)-tetraenes requires higher temperatures (9°C for the first step and 40°C for the second step) and the closure of Z,Z,Z,Z-substrates is even slower, affording the [4.2.0] product directly at 65°C. See: (a) Huisgen, R.; Dahmen, A.; Huber, H. J. Am. Chem. Soc. 1967, 89, 7130. (b) Huisgen, R.; Dahmen, A.; Huber, H. Tetrahedron Lett. 1969, 1461. (c) For a related example and a literature survey, see: Hayashi, R.; Fernandez, S.; Okamura, W. H. Org. Lett. 2002, 4, 851.
15. Thomas, B. E., IV; Evanseck, J. D.; Houk, K. N. J. Am. Chem. Soc. 1993, 115, 4165.
16. Stannane compounds 8 were prepared from the corresponding iododienes 7; see Supporting Information.
17. For each of the entries, the linear tetraene 9 underwent the double closure within the time frame of the coupling experiment (i.e., we never saw linear tetraene or cyclooctatriene in any of these experiments). Nuclear Overhauser experiments confirmed the stereochemical assignments of all products in Table 1.
18. These isomers were not separated. Nevertheless, a NOE experiment on the mixture allowed assignment.