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Synfacts 2022; 18(02): 0115
DOI: 10.1055/s-0041-1737235
DOI: 10.1055/s-0041-1737235
Synthesis of Natural Products and Potential Drugs
Total Synthesis of (±)-Phainanoid A
Xie J,
Liu X,
Zhang N,
Choi S,
Dong G.
*
The University of Chicago, USA
Bidirectional Total Synthesis of Phainanoid A via Strategic Use of Ketones.
J. Am. Chem. Soc. 2021;
143: 19311-19316
DOI: 10.1021/jacs.1c11117.
Bidirectional Total Synthesis of Phainanoid A via Strategic Use of Ketones.
J. Am. Chem. Soc. 2021;
143: 19311-19316
DOI: 10.1021/jacs.1c11117.
Key words
(±)-phainanoid A - dammarane triterpenoid - radical polyene cyclization - semipinacol rearrangement - intramolecular alkenylation
Significance
Dong and co-workers report the total synthesis of (±)-phainanoid A, a dammarane-type triterpenoid featuring a complex scaffold consisting of ten rings and 13 chiral centers.
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Comment
The cyclobutane moiety in J was accessed via Pd-catalyzed intramolecular alkenylation. The five-membered ring in the natural product was achieved with a 1,4-addition, which was followed by homoallylic elimination to form the three-membered ring.
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Publication History
Article published online:
18 January 2022
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