5022-20-8Relevant articles and documents
Synthesis of the Mammea Coumarins. Part 4. Stereochemical and Regiochemical Studies, and Synthesis of (-)-Mammea B/BB
Crombie, Leslie,Jones, Raymond C. F.,Palmer, Christopher J.,Begley, Michael J.
, p. 353 - 358 (2007/10/02)
Acylation of phloroglucinol with (S)-2-methylbutyryl chloride followed by Pechmann condensation with ethyl 3-oxohexanoate, or acylation of 5,7-dihydroxy-4-propylcoumarin with (S)-2-methylbutyryl chloride gave an 8-(S)-acylcoumarin that was C-alkylated to afford natural (-)-mammea B/BB: the configuration of the 2-methylbutyryl moiety in the natural coumarins was thus demonstrated to be (S)-Surangin B was likewise prepared as a mixture of 1'S, 2''S)- and (1'R, 2''S)-stereoisomers.The crystal structure and conformation of a 6-acylcoumarin that establishes the orientation of other synthetic coumarins is reported.
Synthesis of mammeins and surangin A
Crombie,Jones,Palmer
, p. 2929 - 2932 (2007/10/02)
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