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
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.
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.
