Intramolecular ring cleavage of chiral terpenoid-derived oxazinone via asymmetric anti-aldol reaction: Unexpected entry to a N-substituted tetrahydro-1,3-oxazine-2,4-dione derivative

Tetrahedron Letters

Volumn 38, Issue 27, 1997, Pages 4917-4920

  Abbas, Tariq R ^a   Cadogan, J I G ^b   Doyle, Allan A ^a   Gosney, Ian ^a   Hodgson, Philip K G ^c   Howells, Garnet E ^a   Hulme, Alison N ^a   Parsons, Simon ^a   Sadler, Ian H ^a  

^a UNIVERSITY OF EDINBURGH   (United Kingdom)

^b IMPERIAL COLLEGE LONDON   (United Kingdom)

^c Research Laboratory   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

1,3 OXAZINE DERIVATIVE; TERPENOID;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; CONFORMATION; DRUG SYNTHESIS; ISOMERISM; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

EID: 0030912584     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01058-7     Document Type: Article

References (11)

1. For a review, see Cadogan, J.I.G.; Doyle, A.A.; Gosney, I.; Hodgson, P.K.G.; Thorburn, P.; Enantiomer, 1997, 2(2), 81-98.
2. See in particular, Kunz, H.; Ruck, K.; Angew. Chem. Int. Ed. Engl., 1993, 32, 336-358, and references cited therein.
3. Banks, M.R.; Cadogan, J.I.G.; Gosney, I.; Gaur, S.; Hodgson, P.K.G.; Tetrahedron Asymmetry, 1994, 5, 2447-2458.
4. Ref. 2, page 346.
5. Ann, H.K.; Lee, S.; Lim, A.; J. Org. Chem., 1992, 52, 5065-5066.
6. For pertinent references to the synthesis of tetrahydro-1,3-oxazine-2,4-diones, see Barton, D.H.R.; Liu, W.; J. Chem. Soc. Chem. Commun., 1997, 571-572.
7. Banks, M.R.; Blake, A.J.; Cadogan, J.I.G.; Dawson, I.M.; Gosney, I.; Grant, K.J.; Gaur, S.; Hodgson, P.K.G.; Knight, K.S.; Smith, G.W.; Stevenson, D.E.; Tetrahedron, 1992, 48, 7979-8006.
8. See ref. 6, and references cited therein.
9. 4 (M+H) requires 358.20183.
10. Danda, H.; Hansen, M.M.; Heathcock, C.H.; J. Org. Chem., 1990, 55, 173-181.
11. 4 (M+H) requires 358.20183.