Birch reduction of 3,4-dihydro-8-hydroxy-3-methylisocoumarin (Mellein). Expeditious syntheses of (±)-ramulosin and a spruce budworm toxin

Tetrahedron Letters

Volumn 38, Issue 12, 1997, Pages 2071-2072

  Schultz, Arthur G ^a   Li, Yu Jang ^a  

^a Research Rensselaer Polytechnic Institute   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC ANTIBIOTIC; PLANT TOXIN; RAMULOSIN; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; DRUG SYNTHESIS; REACTION ANALYSIS; REDUCTION;

CHORISTONEURA FUMIFERANA; PICEA;

EID: 0031585049     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00296-7     Document Type: Article

References (16)

1. 1. For the Birch reduction-alkylations of 3,4-dihydro-4-alkyl-5-methylisocoumarins, see: Schultz, A. G.; Kirincich, S. J. J. Org. Chem. 1996, 61, 5631-5634.
2. 2. Both enantiomers of mellein occur in nature. For a recent identification of R-(-)-mellein in the culture fluids of the fungus Phoma tracheiphila, see: Parisi, A.; Piattelli, M.; Tringali, C.; Magnano di San Lio, G. Phytochemistry 1993, 32, 865-867. For the isolation of (+)-mellein, see: Patterson, E. L.; Anders, W. W.; Bohonos, N. Experientia 1966, 22, 209; Grove, J. F.; Pople, M. J. Chem. Soc., Perkin Trans. I 1979, 2048.
3. 2. Both enantiomers of mellein occur in nature. For a recent identification of R-(-)-mellein in the culture fluids of the fungus Phoma tracheiphila, see: Parisi, A.; Piattelli, M.; Tringali, C.; Magnano di San Lio, G. Phytochemistry 1993, 32, 865-867. For the isolation of (+)-mellein, see: Patterson, E. L.; Anders, W. W.; Bohonos, N. Experientia 1966, 22, 209; Grove, J. F.; Pople, M. J. Chem. Soc., Perkin Trans. I 1979, 2048.
4. 2. Both enantiomers of mellein occur in nature. For a recent identification of R-(-)-mellein in the culture fluids of the fungus Phoma tracheiphila, see: Parisi, A.; Piattelli, M.; Tringali, C.; Magnano di San Lio, G. Phytochemistry 1993, 32, 865-867. For the isolation of (+)-mellein, see: Patterson, E. L.; Anders, W. W.; Bohonos, N. Experientia 1966, 22, 209; Grove, J. F.; Pople, M. J. Chem. Soc., Perkin Trans. I 1979, 2048.
5. 2O: C, 65.25; H, 7.78. Found: C, 65.17; H, 7.85.
6. 3: C, 65.92; H, 7.74. Found: C, 65.63; H, 7.84.
7. 5. (a) Fried, J.; Abraham, N. A.; Santhanakrishnan, T. S. J. Am. Chem. Soc. 1967, 89, 1044-1045.
8. (b) Radlick, P.; Crawford, H. T. J. Org. Chem. 1972, 37, 1669.
9. 6. Schultz, A. G.; Li, Y.-J. Tetrahedron Lett. 1996, 37, 6511-6514.
10. 7. Stodola, F. H.; Cabot, C.; Benjamin, C. R. Biochem. J. 1964, 93, 92.
11. 8. Kondo, S.; Horiuchi, Y.; Hamada, M.; Takeuchi, T.; Umezawa, H. J. Antibiotics 1979, 32, 1069.
12. 9. For previous total syntheses of ramulosin, see: Enders, D.; Kaiser, A. Synthesis 1996, 209-214 and references cited therein.
13. 3) m/z 185 (M+1), 167,123.
14. 11. For an early example of olefin isomerization during catalytic hydrogenation with Pd/C, see: Sauvage, J. F.; Baker, R. H.; Hussey, A. S. J. Am. Chem. Soc. 1961, 83, 3874-3877.
15. 12. (a) Findlay, J. A.; Buthelezi, S.; Lavoie, R.; Peña-Rodriguez, L.; Miller, J. D. J. Nat. Prod. 1995, 58, 1759.
16. (b) Attempted synthesis of 7 by Mitsonobu reaction of 5 with 4-nitrobenzoic acid gave dehydration to the α,ß-unsaturated lactone (84%).