Total Synthesis of Lapidilectine B Enabled by Manganese(III)‐Mediated Oxidative Cyclization of Indoles. Issue 25 (17th April 2018)

• Record Type: Journal Article
• Authors: Gao, Yang; Fan, Mengyang; Geng, Qixiang; Ma, Dawei
• Is Part Of: Chemistry. Volume 24:Issue 25(2018)
• Page Start: 6547
• Page End: 6550
• Publication Date: 2018-04-17
• Subjects: allenic amine -- indole alkaloid -- oxidative cyclization -- pyrrolidine ring -- ring-expansion; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201801312
• Languages: English
• ISSNs: 0947-6539

Abstract

Abstract: A novel manganese(III)‐mediated oxidative cyclization of readily accessible 1, 2, 3‐trisubstituted indoles is described. This unprecedented method enabled the efficient construction of a complex polycyclic scaffold bearing a spiro‐indoline motif and a lactone moiety in one step. Its synthetic utility was demonstrated in the total synthesis of lapidilectine B (in 18 steps) by employing a strategic regioselective ring‐expansion and a silver‐promoted allenic amine cyclization as the additional key elements. Abstract : Total synthesis of lapidilectine B was achieved using a Mn III ‐mediated oxidative cyclization of a 1, 2, 3‐trisubstrated indole, a ring‐expansion operation, and a silver‐promoted allenic amine cyclization as the key steps.