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May 23, 2006Organic LettersOpen Access

Synthesis of Precursors of the Agalacto (Exo) Fragment of the Quartromicins via an Auxiliary-Controlled Exo-Selective Diels−Alder Reaction

Jun Qi William Roush

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Abstract

[reaction: see text] A direct synthesis of the alpha-hydroxyaldehyde exo-5, a precursor of the exo-spirotetronate subunit of the quartromicins, was achieved through an exo-selective Lewis acid-catalyzed Diels-Alder reaction of dienophile 12a and diene 1.

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Qi et al. (2006) studied this question.

synapsesocial.com/papers/6a6da820e36a167817e021da https://doi.org/10.1021/ol0609208

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Synapse has enriched 5 closely related papers on similar clinical questions. Consider them for comparative context:

1The structures of quartromicins A1, A2, and A3: novel macrocyclic antiviral antibiotics possessing four tetronic acid moietiesOriginal Research · 1991 · 51 citations
2Anti-Human Immunodeficiency Virus (HIV) Activity of the Novel Antiviral Antibiotic Quartromicins which Enhance Inhibitory Effect of 3′-azido-2′,3′-dideoxythymidine (AZT) <i>in vitro</i>In Vitro Study · 1992 · 14 citations
3Partial Stereochemical Assignment of Quartromicins A3 and D3Original Research · 2002 · 13 citations
4Diastereoselective Synthesis of the endo- and exo-Spirotetronate Subunits of the Quartromicins. The First Enantioselective Diels−Alder Reaction of an Acyclic (Z)-1,3-DieneOriginal Research · 2002 · 38 citations
5Studies on the Synthesis of Quartromicins A<sub>3</sub> and D<sub>3</sub>: Synthesis of the Vertical and Horizontal Bis-Spirotetronate FragmentsOriginal Research · 2006 · 22 citations

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