Second generation synthesis of the quartromicin spirotetronic acid subunits via a Claisen rearrangement-intramolecular aldol sequence

Tetrahedron Letters

Volumn 38, Issue 51, 1997, Pages 8785-8788

  Roush, William R ^a,b   Barda, David A ^a  

^a INDIANA UNIVERSITY   (United States)

^b UNIVERSITY OF MICHIGAN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIBIOTIC AGENT; ANTIVIRUS AGENT; QUARTROMICIN DERIVATIVE; TETRONIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; IN VITRO STUDY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030732916     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10416-6     Document Type: Article

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29. Intermediate 29 is more easily prepared via a sequence involving the Lewis acid catalyzed Diels-Alder reaction of a (Z)-diene (related to 5) and α-acetoxy acrolein (Roush, W. R.; Barda, D. A. J. Am. Chem. Soc. 1997, 119, 7402) followed by oxidation of the aldehyde to the methyl ester. Elaboration of 29 to 30 was performed following the sequence described for the conversion of 13 to 4.