An intramolecular Diels-Alder approach to the spirotetronic acid subunits of the quartromicins

Tetrahedron Letters

Volumn 38, Issue 51, 1997, Pages 8781-8784

  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; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; IN VITRO STUDY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030779556     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10415-4     Document Type: Article

References (35)

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34. Spirotetronate 2 was also prepared directly from aldehyde 22 in 63% overall yield by Luche reduction, protection of the allylic alcohol as a TBS ether, and Dieckmann cyclization.
35. The selenide oxidation in the synthesis of 24 was performed under carefully controlled conditions to prevent over-oxidation of the enal to the carboxylic acid, as occurred in the conversion of 17 to 22. Elaboration of the enal intermediate to 24 was performed as summarized in ref. 35 for 22. The yield of 24 was 20% yield for the 10 step sequence from 16.