Stereoselective Syntheses of (+)-Broussonetine D and (+)-Australine via a Functionalized Pyrrolidine from an Extended Chiral 1,3-Oxazine

被引：10

作者：

Myeong, In-Soo ^{[1
]}

Ham, Won-Hun ^{[1
,2
]}

机构：

[1] Sungkyunkwan Univ, Sch Pharm, Seobu Ro 2066, Suwon 16419, Gyeonggi Do, South Korea

[2] Yonsung Fine Chem Co Ltd, Sujeong Ro 207, Hwaseong Si 18581, Gyeonggi Do, South Korea

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2019年 / 2019卷 / 05期

关键词：

Alkaloids; Asymmetric synthesis; Metathesis; Allylation; Diastereoselectivity; METATHESIS-TRANSANNULAR CYCLIZATION; 1ST TOTAL-SYNTHESIS; GLYCOSIDASE INHIBITION; FORMAL SYNTHESIS; NATURAL OCCURRENCE; AUSTRALINE; GLUCOSIDASE; ALKALOIDS; CASTANOSPERMINE; PYRROLIZIDINES;

D O I：

10.1002/ejoc.201801552

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The asymmetric syntheses of (+)-broussonetine D and (+)-australine have been achieved via a functionalized pyrrolidine obtained from an extended chiral 1,3-oxazine. The key steps include pyrrolidine formation by oxazine cleavage and diastereoselective allylation to a pyrrolidine aldehyde. (+)-Broussonetine D and (+)-australine were synthesized from anti,syn,syn-oxazine, in six steps, with an overall yield of 22.2 %, and in seven steps, with an overall yield of 33.2 %.

引用

页码：1077 / 1082

页数：6

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