Department of Applied Chemistry, Faculty of Science and Technology, Keio University, 3-14-1, Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan.
Org Lett. 2015 Apr 17;17(8):1946-9. doi: 10.1021/acs.orglett.5b00661. Epub 2015 Mar 27.
A general synthetic route toward a diazatricyclic core common to the madangamine family is described. Ring-closing metathesis and palladium-catalyzed cycloisomerization provided the cis-fused diazadecalin structure, accompanied by formation of the N-Boc-enamine, which was utilized as an N-acyliminium ion equivalent. Direct cyclization from the N-Boc-enamine was achieved through the in situ formation of an N,O-acetal.
描述了一种通向马当胺家族共有的二氮杂三环核心的一般合成途径。环 closing 复分解和钯催化环化异构化提供了顺式稠合的二氮杂十氢化萘结构，同时形成了 N-Boc-烯胺，可作为 N-酰亚胺离子等价物使用。通过原位形成 N,O-缩醛，从 N-Boc-烯胺直接进行环化。
