83.Total Synthesis of Aplykurodinone-1

Gang Liu, Guangjian Mei, Runwen Chen, Haina Yuan, Zhen Yang*, and Chuang-chuang Li*

Org. Lett.201416, 4380

The concise total synthesis of aplykurodinone-1 with an unusual cis-fused hydrindane moiety has been accomplished without the need for any protecting group chemistry using a unique SmI2 mediated reductive cascade cyclization reaction and a direct cuprate mediated 1,4-addition. This work represents the first example of the use of a SmI2-mediated intramolecular cascade cyclization reaction between “halide, alkene and aldehyde” groups.

ol-2014-02220r_0007