An enantioselective approach to the Securinega alkaloids: the total synthesis of (+)-norsecurinine and (+)-allonorsecurinine

TETRAHEDRON

卷:66

Article

Medeiros, Matthew R.²  Wood, John L.¹ 

[1] Colorado State Univ, Dept Chem, Ft Collins, CO 80523 USA

[2] Yale Univ, Dept Chem, New Haven, CT 06520 USA

关键词: Securinga Alkaloids;    Norsecurinine;    Allonorsecrinine;    Total Synthesis;    Rhodium Carbenoid;    Claisen rearrangement;   

DOI  :  10.1016/j.tet.2010.03.015

来源: Elsevier

【 摘 要 】

Total syntheses of (+)-norsecurinine and (+)-allonorsecurinine are described that utilize a rhodium carbenoid-initiated O-H insertion/Claisen rearrangement/1,2-allyl migration domino process for the stereoselective introduction of the tertiary alcohol moiety. Overall the employed strategy is flexible and will allow access to other members of the Securinega family of alkaloids. (C) 2010 Elsevier Ltd. All rights reserved.

【 授权许可】

Free