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Synfacts 2022; 18(10): 1059
DOI: 10.1055/s-0042-1752951
DOI: 10.1055/s-0042-1752951
Synthesis of Natural Products
Total Synthesis of Indolizidine Alkaloid (±)-Bipolamine I
Qiu X,
Pierce JG.
*
NC State University, Raleigh, USA
Total Synthesis of Bipolamine I.
J. Am. Chem. Soc. 2022;
144: 12638-12641
DOI: 10.1021/jacs.2c06015.
Total Synthesis of Bipolamine I.
J. Am. Chem. Soc. 2022;
144: 12638-12641
DOI: 10.1021/jacs.2c06015.
Key words
(±)-bipolamine I - indolizidine alkaloids - ring-closing metathesis - Barton–McCombie deoxygenation - samarium(II) iodide
Significance
Pierce and Qiu report the first total synthesis of (±)-bipolamine I. The polypyrrole-containing subclass of indolizidine alkaloids is active against a variety of Gram-positive and -negative bacterial pathogens.
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Comment
Cycloheptenol N is accessed in nine steps from acid A. The sequence features allylation of I with K, followed by ring-closing metathesis of L. MnO2 oxidation of N results in formation of bridged ether O, and treatment with SmI2 leads to hemiacetal Q. A final Barton deoxygenation affords (±)-bipolamine I.
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Publication History
Article published online:
20 September 2022
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