Stereocontrolled construction of either stereoisomer of 12-oxatricyclo[6.3.1.02,7]dodecanes using prins-pinacol reactions

Organic Letters

Volumn 6, Issue 21, 2004, Pages 3853-3856

  Overman, Larry E ^a   Velthuisen, Emile J ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ADAMANTANE; DODECANE;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; PHASE TRANSITION; PINACOL REARRANGEMENT; REACTION ANALYSIS; RING OPENING; STEREOCHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ALKANES; CRYSTALLOGRAPHY, X-RAY; CYCLIZATION; STEREOISOMERISM;

EID: 7044229825     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0482745     Document Type: Article

References (16)

1. For a recent review, see: Overman, L. E.; Pennington, L. D. J. Org. Chem. 2003, 68, 7143-7157.
2. Zhang, Y.; Wang, T.; Pei, Y.; Hua, H.; Feng, B. J. Antibiot. 2002, 55, 693-695.
3. Maurer, B.; Hauser, A. Helv. Chim. Acta 1983, 66, 2223-2235.
4. This strategy has been employed widely in the synthesis of alkaloids containing the isoindolone unit such as cytochalasin D and aspochalasin C; see: (a) Harkin, S. A.; Jones, R. H.; Tapolczay, D. J.; Thomas, E. J. Chem. Soc., Perkin. Trans. 1 1989, 489-497. (b) Craven, A. P.; Dyke, H. J.; Thomas, E. J. Tetrahedron 1989, 45, 2417-2429. (c) Thomas, E. J.; Watts, J. P. Chem. Soc., Perkin. Trans, 1 1999, 3285-3290.
5. This strategy has been employed widely in the synthesis of alkaloids containing the isoindolone unit such as cytochalasin D and aspochalasin C; see: (a) Harkin, S. A.; Jones, R. H.; Tapolczay, D. J.; Thomas, E. J. Chem. Soc., Perkin. Trans. 1 1989, 489-497. (b) Craven, A. P.; Dyke, H. J.; Thomas, E. J. Tetrahedron 1989, 45, 2417-2429. (c) Thomas, E. J.; Watts, J. P. Chem. Soc., Perkin. Trans, 1 1999, 3285-3290.
6. This strategy has been employed widely in the synthesis of alkaloids containing the isoindolone unit such as cytochalasin D and aspochalasin C; see: (a) Harkin, S. A.; Jones, R. H.; Tapolczay, D. J.; Thomas, E. J. Chem. Soc., Perkin. Trans. 1 1989, 489-497. (b) Craven, A. P.; Dyke, H. J.; Thomas, E. J. Tetrahedron 1989, 45, 2417-2429. (c) Thomas, E. J.; Watts, J. P. Chem. Soc., Perkin. Trans, 1 1999, 3285-3290.
7. For reviews of Prins cyclizations, see: (a) Arundale, E.; Mikeska, L. A. Chem. Rev. 1952, 52, 505-555. (b) Snider, B. B. In The Prins Reaction and Carbonyl Ene Reactions; Trost, B. M., Fleming, I., Heathcock, C. H., Ed.; Pergamom Press: New York, 1991; Vol. 2, pp 527-561.
8. For reviews of Prins cyclizations, see: (a) Arundale, E.; Mikeska, L. A. Chem. Rev. 1952, 52, 505-555. (b) Snider, B. B. In The Prins Reaction and Carbonyl Ene Reactions; Trost, B. M., Fleming, I., Heathcock, C. H., Ed.; Pergamom Press: New York, 1991; Vol. 2, pp 527-561.
9. Barton, D. H. R.; Bashiardes, G.; Fourrey, J.-L. Tetrahedron 1988, 44, 147-162.
10. Jurczak, J.; Bauer, T.; Tetrahedron 1986, 42, 5045-5052.
11. 1H NMR analysis).
12. Crystallographic data for this compound was deposited at the Cambridge Crystallographic Data Centre; CCDC numbers: 14, 249137; 18, 249133; 21, 249132; 29, 249135; 31, 249134; 37, 249136.
13. Smith, C. W.; Norton, D. G.; Ballard, S. A. J. Am. Chem. Soc. 1951, 73, 5270-5272.
14. Mancuso, A. J.; Huang, S.; Swern, D. J. Org. Chem. 1978, 43, 2480-2482.
15. A coupling of 4.2 Hz is observed between the corresponding hydrogens of 17.
16. The ratio of 35/36 in this case was 1:1.