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• W3206096790 abstract "• The BC-rings of canonical SL was constructed by the acid-mediated cascade cyclization. • An 18-oxocarlactonoate derivative was successfully converted to rac -orobanchols. • The cascade cyclization might be based on the conrotatory 4π-electrocyclic reaction. • The cyclization demonstrated “in flask” may be analogous to that in planta . Strigolactones, a class of apocarotenoids, are known to function as rhizosphere semiochemicals and plant hormones. Canonical strigolactones consist of a tricyclic lactone (ABC-rings) and a butenolide moiety (D-ring), and their biosynthesis has been extensively studied. However, the process of BC-ring formation is yet to be clarified. The conversion of an 18-oxocarlactonoate derivative into racemic orobanchols was performed in the same way as in our previous study, which demonstrated that the BC-ring formation is possible “in flask” via acid-mediated cascade cyclization. The results strongly suggested that the mechanism of acid-mediated BC-ring formation may be based on the conrotatory electrocyclic reaction, and may provide significant insights into the process of BC-ring formation in strigolactone biosynthesis." @default.
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• W3206096790 date "2021-11-01" @default.
• W3206096790 modified "2023-10-03" @default.
• W3206096790 title "Synthesis of racemic orobanchols via acid-mediated cascade cyclization: Insight into the process of BC-ring formation in strigolactone biosynthesis" @default.
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• W3206096790 doi "https://doi.org/10.1016/j.tetlet.2021.153469" @default.
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