Phuong Lien Trinh

Bio: Phuong Lien Trinh is an academic researcher. The author has contributed to research in topics: Absolute configuration & Indole alkaloid. The author has an hindex of 1, co-authored 1 publications receiving 8 citations.

Absolute Configuration of the Indole Alkaloid (‐)‐Mehranine Hydrobromide

Abstract: The structure including the absolute configuration of the indole alkaloid (-)-mehranine hydrobromide (1·HBr) has been assigned by X-ray analysis. This result gave the possibility to assign the absolute configurations of some related alkaloids

A Concise and Versatile Double‐Cyclization Strategy for the Highly Stereoselective Synthesis and Arylative Dimerization of Aspidosperma Alkaloids

Abstract: The monoterpene indole alkaloids represent the largest family of alkaloid natural products whose more than 2,000 members display a broad range of chemical diversity and potent biological activity.1 The structural challenges presented by this family have long been a source of interest, resulting in the development of a variety of inventive synthetic strategies to access various family members. The biogenetically related natural alkaloids N-methylaspidospermidine (1), N-methylquebrachamine (2), and tabernaebovine (3) represent the aspidosperma subfamily of monoterpene indole alkaloids (Figure 1).2-5 The dimeric alkaloid 3, isolated from Tabernaemontana bovina in 1998,2e has a fascinating molecular constitution that exhibits a unique C2–C15′ linkage between two pentacyclic aspidosperma skeletons. While elegant strategies for synthesis of other dimeric monoterpene indole alkaloids have been reported,5 no synthetic solution to the distinctive C2–C15′ union present in 3 exists. As an outgrowth of our laboratory's studies concerning electrophilic amide activation,6 we report a concise and convergent strategy for the enantioselective synthesis of alkaloids (–)-1, (+)-2, and dimeric (+)-dideepoxytabernaebovine (4).

Concise and enantioselective total synthesis of (-)-mehranine, (-)-methylenebismehranine, and related Aspidosperma alkaloids.

Abstract: We report an efficient and highly stereoselective synthetic strategy for the synthesis of aspidosperma alkaloids based on the transannular cyclization of a chiral lactam precursor. Three new stereocenters are formed in this key step with excellent level of diastereoselection due to the conformational bias of the cyclization precursor, leading to a versatile pentacyclic intermediate. A subsequent stereoselective epoxidation followed by a mild formamide reduction enabled the first total synthesis of the aspidosperma alkaloids (−)-mehranine and (+)-(6S,7S)-dihydroxy-N-methylaspidospermidine. A late-stage scandium trifluoromethanesulfonate-mediated dimerization of (−)-mehranine enabled the first total synthesis of (−)-methylenebismehranine.

Synthesis of vinca alkaloids and related compounds. 100. Stereoselective oxidation reactions of compounds with the aspidospermane and quebrachamine ring system. First synthesis of some alkaloids containing the epoxy ring.

Abstract: The first syntheses of the alkaloids (−)-mehranine (3), (+)-voaphylline/conoflorine (4), (+)-Na-methylvoaphylline/hecubine (5), and (−)-lochnericine (2) were achieved by stereoselective epoxidation starting from (−)-tabersonine (1), through intermediates with the aspidospermane and quebrachamine skeleton.

A Review on Recent Developments in Syntheses of the Post-Secodine Indole Alkaloids. Part I: The Primary Alkaloid Types

Abstract: This first part of a planned review on developments in the field of total and formal total synthesis of the post-secodine indole alkaloids concentrates on primary alkaloid types. It reviews the synthesis of secodine, aspidospermane, pseudoaspidospermane and ibogane alkaloids; andranginine is also included. It covers the literature from 1992-1993 up to approximately May 2004. A review with 179 references.

Enantioselektive Totalsynthese von (−)‐Mehranin, (−)‐Methylenbismehranin und verwandten Aspidosperma‐Alkaloiden

Abstract: Wir berichten uber eine effiziente und hochstereoselektive Strategie zur Synthese von Aspidosperma-Alkaloiden, die auf der transannularen Cyclisierung einer chiralen Lactamvorstufe basiert. Aufgrund der bevorzugten Konformation der Cyclisierungsvorstufe werden in diesem Schlusselschritt drei neue Stereozentren des resultierenden, vielseitigen, pentacyclischen Intermediats mit exzellenter Diastereoselektivitat aufgebaut. Eine anschliesende stereoselektive Epoxidierung mit nachfolgender Formamidreduktion unter milden Bedingungen ermoglichte die erste Totalsynthese der Aspidosperma-Alkaloide (−)-Mehranin und (+)-(6S,7S)-Dihydroxy-N-methylaspidospermidin. Eine abschliesende, Scandiumtrifluormethansulfonat-vermittelte Dimerisierung von (−)-Mehranin fuhrte zur ersten Totalsynthese von (−)-Methylenbismehranin.