Synthetic approach to seco-tetracenomycin natural products saccharothrixone A–C

• Published in: Tetrahedron letters Vol. 59; no. 20; pp. 1970 - 1973
• Main Authors: Chinta, Bhavani Shankar, Sanapa, Harikrishna, Vasikarla, Kamala Prasad, Baire, Beeraiah
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 16.05.2018; Elsevier
• Subjects: Alkynes; Chemistry; Chemistry, Organic; Cycloadditions; Natural products; Phthalides; Physical Sciences; Science & Technology; Total synthesis; Phthalides; Cycloadditions; Natural products; Total synthesis; Alkynes; REARRANGEMENT; DIELS-ALDER REACTIONS; 4+2 CYCLOADDITION REACTIONS
• ISSN: 0040-4039; 1873-3581
• DOI: 10.1016/j.tetlet.2018.04.031

[Display omitted] •This report represents the first synthetic approach to the tetracenomycin natural products saccharothrixones A–C.•Generation of a small library of diversely functionalized tetracyclic systems of seco-tetracenomycins.•Mild and short synthetic approach for the frame work generation (4–5 steps).•A thermal dehydro Diels-Alder reaction of an arenyne-alkyne unit has been utilized as the key synthetic step.•An approach for the synthesis of poly-hydroxyl tetracyclic system has also been described. Design and development of first synthetic approach to the functionalized tetracyclic framework of structurally novel seco-tetracenomycin natural products saccharothrixones A–C has been reported. A thermal dehydro Diels-Alder reaction of an arenyne-alkyne unit has been utilized as the key synthetic step. This strategy has been extended for the generation of a small library of diversely functionalized tetracyclic systems of seco-tetracenomycins. An approach for the synthesis of poly-hydroxyl tetracyclic system has also been described. This report represents the first synthetic approach to the tetracenomycin natural products saccharothrixones A–C.