A dearomative ipso-iodocyclization/desymmetrization sequence leading to optically active tricyclic piperazine scaffolds

被引：13

作者：

Okitsu, Takashi ^{[1
]}

Horike, Arisa ^{[1
]}

Shimazawa, Natsumi ^{[1
]}

Wada, Akimori ^{[1
]}

机构：

[1] Kohe Pharmaceut Univ, Higashinada Ku, 4-19-1 Motoyamakita, Kobe, Hyogo 6588558, Japan

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2020年 / 18卷 / 18期

关键词：

MICHAEL CASCADE REACTION; ETHOXYETHYL ETHERS; EFFICIENT SYNTHESIS; CHEMICAL SPACE; IODOCYCLIZATION; CYCLIZATION; HALOCYCLIZATION; CONSTRUCTION; FERMENTATION; ALKALOIDS;

D O I：

10.1039/d0ob00510j

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Dearomative ipso-iodocyclization of 4-(1-ethoxyethoxy)-N-propargylanilines leading to 1-azaspiro[4.5]deca-3,6,9-trien-8-ones has been developed. This reaction is characterized by the yield of fewer toxic byproducts and is conducted by a more user-friendly protocol compared to other reported methods. The synthetic application of these spiro products was demonstrated by transformation of the iodo component into other functionalities. The desymmetrization of the resulting cyclohexadienones was also achieved by the diastereoselective aza-Michael addition of internal amino acid moieties to yield tricyclic piperazine scaffolds with two newly formed contiguous chiral centers.

引用

页码：3501 / 3511

页数：11