Stereoselective addition of Grignard reagents to sulfinimines derived from tartrate diol (threitol): Generation of chiral building blocks for the collective total synthesis of lentiginosine, conhydrine and methyldihydropalustramate

TETRAHEDRON

卷:75

Article

Prasad, Kavirayani R.¹  Rangari, Vipin Ashok¹ 

[1] Indian Inst Sci, Dept Organ Chem, Bangalore 560012, Karnataka, India

关键词: Sulfinimines;    Chiral pool;    Stereoselective addition;    Total synthesis;    Alkaloids;   

DOI  :  10.1016/j.tet.2019.130496

来源: Elsevier

【 摘 要 】

A systematic investigation of the addition of Grignard reagents to sulfinimines derived from tartaric acid diol was undertaken. It was observed that the chirality of the inherent tartrate moiety influences the diastereoselectivity of the resultant sulfinamides formed in the reaction. The formed products serve as excellent building blocks for the synthesis of natural products. This has been demonstrated in the collective total synthesis of lentiginosine, (+)-alpha-conhydrine and methyldihydropalustramate. (C) 2019 Elsevier Ltd. All rights reserved.

【 授权许可】

Free