School of Chemistry, University of Nottingham, University Park, Nottingham NG7 2RD, United Kingdom.
Org Lett. 2012 Mar 16;14(6):1484-7. doi: 10.1021/ol300221e. Epub 2012 Feb 27.
The total synthesis of (±)-mevashuntin, a structurally unique naturally occurring pyrano-naphthoquinone-thiazolone, is described. The route is centered upon a late stage regioselective Diels-Alder reaction between two highly functionalized components, as well as an improved protocol for the one pot synthesis of benzothiazolones from ortho-bromoaryl isothiocyanates. The strategy results in a highly convergent route, providing access to the natural product in 11 steps from 3-(4-methoxyphenoxy)propanol and confirming its relative stereochemistry.
（±）-Mevashuntin 是一种结构独特的天然吡喃萘醌噻唑啉，本文描述了它的全合成。该路线以晚期区域选择性 Diels-Alder 反应为中心，涉及两个高度官能化的组分，以及改进的邻溴芳基异硫氰酸酯一锅法合成苯并噻唑啉的方法。该策略得到了一条高度收敛的路线，从 3-（4-甲氧基苯氧基）丙醇出发，经过 11 步反应即可获得天然产物，并确定了其相对立体化学。
