Self-condensation of activated malonic acid half esters: A model for the decarboxylative Claisen condensation in polyketide biosynthesis

Tetrahedron Letters

Volumn 44, Issue 40, 2003, Pages 7499-7502

  Ryu, Youngha ^a   Scott, A Ian ^a  

^a TEXAS A AND M UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1,3 ACETONE DICARBOXYLIC ACID DIESTER; ESTER DERIVATIVE; MALONIC ACID DERIVATIVE; METAL CHELATE; N HYDROXYSUCCINIMIDYL ESTER; POLYKETIDE; SOLVENT; SUCCINIMIDE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BIOSYNTHESIS; CLAISEN CONDENSATION; DECARBOXYLATION; POLYMERIZATION;

EID: 0042836556     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.08.014     Document Type: Article

References (21)

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11. -: 307.1915; found: 307.1904.
12. 4 and evaporated in vacuo to provide a crude mixture.The pure product was obtained by a silica gel column chromatography.
13. 1,3-Acetonedicarboxylic acid diesters have been extensively used as building blocks for more extended carbocyclic structures such as polyquinenes and steroid skeletons by the Weiss reaction or other condensation reactions. For examples, see: (a) Gupta, A. K.; Fu, X.; Snyder, J. P.; Cook, J. M. Tetrahedron 1991, 23, 3665; (b) Danishefsky, S.; Crawley, L. S.; Solomon, D. M. ; Heggs, P. J. Am. Chem. Soc. 1971, 93, 2356.
14. 1,3-Acetonedicarboxylic acid diesters have been extensively used as building blocks for more extended carbocyclic structures such as polyquinenes and steroid skeletons by the Weiss reaction or other condensation reactions. For examples, see: (a) Gupta, A. K.; Fu, X.; Snyder, J. P.; Cook, J. M. Tetrahedron 1991, 23, 3665; (b) Danishefsky, S.; Crawley, L. S.; Solomon, D. M. ; Heggs, P. J. Am. Chem. Soc. 1971, 93, 2356.
15. 2).
16. -: 417.2646; found: 417.2620.
17. -: 553.3898; found: 553.3831.
18. For reviews of reactions in aqueous amphiphilic self-assembling systems, see: (a) Lindstrom, U. M. Chem. Rev. 2002, 102, 2751; (b) Engberts, J. B. F. N. ; Blandamer, M. J. Chem. Commun. 2001, 1701-1708.
19. For reviews of reactions in aqueous amphiphilic self-assembling systems, see: (a) Lindstrom, U. M. Chem. Rev. 2002, 102, 2751; (b) Engberts, J. B. F. N. ; Blandamer, M. J. Chem. Commun. 2001, 1701-1708.
20. It is likely that the final product was already formed during the reaction rather than work-up according to a time course study by silica gel thin layer chromatographic analysis.
21. As we could expect from the suggested mechanism, a cross-condensation between two different MAHOs yielded one cross-condensation product and two self-condensation products in almost equal distribution. For instance, a reaction of 1a and 1h with TSTU and DPEA in DMF provided 1, 3-acetonedicarboxylic acid benzyl tert-butyl ester in 34% yield along with 2a and 2h in 25 and 26% yield, respectively. A slightly higher yield of the cross-condensation product is probably due to a slight difference in reactivities of two NHS intermediates generated from their corresponding MAHOs.