title: Total synthesis of (±)-sacidumlignans D and A through Ueno-Stork radical cyclization reaction.
abstract: Efficient synthesis of (±)-sacidumlignan D (4) has been successfully achieved employing Ueno-Stork radical cyclization of α-bromo acetal 21 as a key step. Two synthetic approaches for the symmetrical diaryl ketone 19 have been discussed in detail. Notably, sacidumlignan A (1) can be also efficiently synthesized in only 7 steps with 25% overall yield, where acid triggered tandem reaction starting from analogous Ueno-Stork cyclization product 27 played an important role. Moreover, potentially biomimetic conversion from (±)-sacidumlignan D (4) to sacidumlignan A (1) could be realized.
authors: State Key Laboratory of Applied Organic Chemistry and College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, People's Republic of China.
authors: Jian-Jian
authors: JJ
authors: Zhang
authors: Chang-Song
authors: CS
authors: Yan
authors: Yu
authors: Y
authors: Peng
authors: Zhen-Biao
authors: ZB
authors: Luo
authors: Xiao-Bo
authors: XB
authors: Xu
authors: Ya-Wen
authors: YW
authors: Wang
mesh_terms: D060326:Chemistry Techniques, Synthetic; D003500:Cyclization; D017705:Lignans / Q000138:chemical synthesis* / Q000737:chemistry*; D008958:Models, Molecular; D008968:Molecular Conformation
chemical_list: D017705:Lignans; C583849:sacidumlignan A; C561165:sacidumlignan D