Wang Bian-Lin, Gao Hai-Tao, Li Wei-Dong Z
†State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, P. R. China.
‡Innovative Drug Research Centre, Chongqing University, Chongqing 401331, P. R. China.
J Org Chem. 2015 May 15;80(10):5296-301. doi: 10.1021/acs.joc.5b00365. Epub 2015 Apr 29.
The first asymmetric total synthesis of (+)-iresin (4), an historically important ent-Drimane sesquiterpene lactone, was realized from aldehyde 3 via cyclic orthoester 6 in 5 steps. Notable transformations in this synthesis include a tandem trifluoroperacetic acid (TFPAA)-mediated Baeyer-Villiger oxidation-olefin epoxidation-epoxy ester cyclization, regioselective Burgess dehydration, and regioselective Fétizon oxidative lactonization.
(+)-异树脂（4）是一种具有历史意义的对映-杜松烷倍半萜内酯，首次通过环状原酸酯6由醛3经5步实现了其不对称全合成。该合成中的显著转化包括串联的三氟过氧乙酸（TFPAA）介导的拜耳-维利格氧化-烯烃环氧化-环氧酯环化、区域选择性的伯吉斯脱水反应以及区域选择性的费蒂松氧化内酯化反应。
