The shikimate pathway. Part 8.1 Synthesis of (-)-3(R)-amino-4(R),5(R)-dihydroxy-1-cyclohexene-1-carboxylic acid: The 3(R)-amino analogue of (-)-shikimic acid

Tetrahedron

Volumn 52, Issue 25, 1996, Pages 8565-8580

  Adams, Harry ^a   Bailey, Neil A ^a   Brettle, Roger ^a   Cross, Richard ^a   Frederickson, Martyn ^a,c   Haslam, Edwin ^a   MacBeath, Fiona S ^a   Davies, Gareth M ^b  

^a UNIVERSITY OF SHEFFIELD   (United Kingdom)

^b ASTRAZENECA   (United Kingdom)

^c UNIVERSITY OF LEEDS   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

SHIKIMIC ACID; SHIKIMIC ACID DERIVATIVE;

ARTICLE; BIOSYNTHESIS; CATALYSIS; CONTROLLED STUDY; NONHUMAN; PHYTOCHEMISTRY; PLANT SEED; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 0029951044     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00398-5     Document Type: Article

References (20)

1. Part 7. Richards, T.I.; Layden, K.; Warminski, E.E.; Milburn, P.J.; Haslam, E. J. Chem. Soc., Perkin Trans. 1, 1987, 2765-2773.
2. Haslam E. Shikimic acid: Metabolism and Metabolites; John Wiley and Sons: Chichester, 1993.
3. Campbell, M.M.; Sainsbury, M.; Searle, P.A. Synthesis, 1993, 179-193.
4. Grossbard, E.; Atkinson, D. The Herbicide Glyphosate; Butterworths: Boston, 1985.
5. Brettle, R.; Cross, R.; Frederickson, M.; Haslam, E.; Davies, G.M. Bioorg. Med. Chem. Lett., 1996, 6, 291-294.
6. Marvell, E.N.; Joncich, M.J. J. Am. Chem. Soc., 1951, 73, 973-975.
7. Wright, J.B. J. Am. Chem. Soc., 1955, 77, 4883-4884.
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9. Whole star aniseed was obtained from Brome and Schimmer Ltd., Romsey Industrial Estate, Romsey, Hamphire, U.K., SO51 0HR.
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11. Grewe, R.; Jensen, H.; Schnoor, M. Chem. Ber., 1956, 89, 898-905.
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13. Hedgley, E.J.; Fletcher Jr., H.G. J. Am. Chem. Soc., 1962, 84, 3726-3731.
14. Hedgley, E.J.; Fletcher Jr., H.G. J. Am. Chem. Soc., 1963, 85, 1615-1617.
15. Crystals of bromide 12 suitable for X-ray crystallographic studies were obtained by crystallization from ethyl acetate. Supplementary data for the X-ray crystallographic study of 12 including tables of bond lengths and angles have been deposited with the Director of the X-ray Crystallographic Database, Cambridge and are available upon request.
16. Baltas, M.; Despeyroux, P.; Gorrichon, L. Bioorg. Med. Chem. Lett., 1993, 3, 1447-1452.
17. For the synthesis of the 5(R)-amino analogue of (-)-shikimic acid and its derivatives see: Pansegrau, P.D.; Anderson, K.S.; Widlanski, T.; Ream, J.E.; Sammons, R.D.; Sikorski, J.A.; Knowles, J.R. Tetrahedron Lett., 1991, 32, 2589-2592.
18. Staudinger , H.; Meyer, J. Helv. Chim. Acta, 1919, 2, 635-646.
19. 11 allowing the isolation of large quantities of product 1 (>50 g) with very low levels of impurities.
20. Peace, B.W.; Carman, F.; Wulfman, D.S. Synthesis, 1971, 658-661.