A unified and straightforward total synthesis of (+)-porantheridine and (−)-6-epi-porantheridine. Issue 10 (4th April 2019)

• Record Type: Journal Article
• Authors: Wang, Jiwu; Li, Wang; Liu, Lixia; Wang, Bo; Zhou, Yi; Huang, Shuangping; Wang, Xiaoji
• Is Part Of: Organic chemistry frontiers. Volume 6:Issue 10(2019)
• Page Start: 1599
• Page End: 1602
• Publication Date: 2019-04-04
• Subjects: Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1039/c8qo01398e
• Languages: English
• ISSNs: 2052-4110

Abstract

Abstract : A unified asymmetric total synthesis of (+)-porantheridine and (−)-6- epi -porantheridine has been accomplished from a common intermediate. Abstract : A unified asymmetric total synthesis of (+)-porantheridine and (−)-6- epi -porantheridine has been accomplished. The two molecules were prepared via a Horner–Wadsworth–Emmons/aza-Michael addition reaction or diastereoselective nucleophilic substitution of 2-methoxypiperidine from a common intermediate, respectively. The key features of the unified synthetic strategy also included an asymmetric addition of silyl dienolate to sulfinylimine, substrate-controlled reduction, Wacker oxidation and TFA-promoted cyclization.