Kobayashi Toyoharu, Hayano Futaba, Kamiya Akinobu, Kawamoto Yuichiro, Ito Hisanaka
School of Life Sciences, Tokyo University of Pharmacy and Life Sciences, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan.
Org Lett. 2024 Jun 21;26(24):5105-5109. doi: 10.1021/acs.orglett.4c01384. Epub 2024 Jun 7.
The asymmetric total synthesis of (+)-lemnardosinane A, a rare rearranged sesquiterpenoid, has been accomplished from ()-carvone. Key features of the synthesis are the formation of a bicyclo[3.3.1]nonane skeleton using the intramolecular aldol reaction, the stereoselective introduction of an alkyne group, and the stereoselective formation of a tricyclic skeleton via intramolecular pinacol coupling.