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Synfacts 2022; 18(11): 1169
DOI: 10.1055/s-0042-1752997
DOI: 10.1055/s-0042-1752997
Synthesis of Natural Products
Total Synthesis of the Grayanoid (+)-Mollanol A
Wang Y,
Zhao R,
Yang M.
*
Lanzhou University, P. R. of China
Total Synthesis of Mollanol A.
J. Am. Chem. Soc. 2022;
144: 15033-15037
DOI: 10.1021/jacs.2c06981
Total Synthesis of Mollanol A.
J. Am. Chem. Soc. 2022;
144: 15033-15037
DOI: 10.1021/jacs.2c06981
Key words
(+)-Mollanol A - grayanoid - Conia–ene cyclization - Kharasch–Sosnovsky reaction - Stille cross–coupling - vinylogous aldol addition - oxa–Michael addition
Significance
Yang and co-worker report the first and enantioselective total synthesis of mollane-type grayanoid (+)‑mollanol A. The natural product has an unprecedented C-nor-D-homograyane carbon framework with an oxabicyclo[3.2.1]core.
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Comment
The total synthesis of (+)-mollanol A features a convergent strategy. Fragment E and L are connected in a Stille cross–coupling. Subsequent vinylogous aldol addition, followed by conjugate addition allows for a quick and efficient assembly of the entire carbon framework.
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Publication History
Article published online:
18 October 2022
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