Formal total synthesis of (±)-martinellic acid

He, Yan‐Ping; Moningka, Remond; Lovely, Carl J.

doi:10.1016/j.tetlet.2005.01.004

Cited by 25 publications

(2 citation statements)

References 28 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Over the past decade, considerable effort has been devoted to the synthesis of the martinella alkaloids. – The pyrrolo[3,2- c ]quinoline core of the martinella alkaloids has been prepared by several synthetic routes including the imino Diels−Alder reaction of 2-pyrroline and an N -arylimine, the inter- and intramolecular 1,3-dipolar cycloadditions of azomethine ylides to olefins, Heck reactions under palladium catalysis, intramolecular radical cyclizations between aryl iodides and pyrroles, Fischer-type cycloaddition, and others …”

mentioning

confidence: 99%

Total Synthesis of (−)-Martinellic Acid via Radical Addition−Cyclization−Elimination Reaction

et al. 2008

View full text Add to dashboard Cite

The asymmetric total synthesis of martinellic acid, the first pyrrolo[3,2-c]quinoline alkaloid found in nature, is described. Three key steps in our synthesis of (-)-martinellic acid are the Bu(3)SnH-promoted radical addition-cyclization-elimination (RACE) reaction of an oxime ether with an alpha,beta-unsaturated ester to generate the pyrrolo[3,2-c]quinoline core, a chemoselective lactam carbonyl reduction, and guanidinylation under Mitsunobu reaction conditions. The key radical cyclization has also been investigated by using SmI(2). (-)-Martinellic acid was synthesized from commercially available methyl 4-bromo-3-methylbenzoate in fewer steps than previous syntheses and in an improved overall yield.

show abstract

mentioning

confidence: 99%

Total Synthesis of (−)-Martinellic Acid via Radical Addition−Cyclization−Elimination Reaction

et al. 2008

View full text Add to dashboard Cite

show abstract

“…[98][99][100][101][102][103][104][105][106][107][108][109][110][111][112] The key features of our synthesis are the tandem Michael-Aldol reaction 113,114) using an anthranilaldehyde and a Michael acceptor developed by us and the stereoselective formation of the pyrroloquinoline moiety as outlined in Chart 31.…”

Section: Enantioselective Synthesis Of Martinellic Acidmentioning

confidence: 99%

Development of New Methods in Organic Synthesis and Their Applications to the Synthesis of Biologically Interesting Natural Products

Hamada

2012

CHEMICAL & PHARMACEUTICAL BULLETIN

View full text Add to dashboard Cite

2,6-Dimethyl-9-Aryl-9-phosphabicyclo[3.3.1]nonanes (9-PBN and 9-NapBN) and the chiral diaminophosphine oxides (DIAPHOXs) derived from aspartic acid have been introduced as useful ligands and preligands, respectively, for transition metal-catalyzed asymmetric synthesis. anti-Selective asymmetric hydrogenation of α-amino-β-ketoesters using Ru-, Rh-, Ir-, and Ni-catalysts through dynamic kinetic resolution have been developed for the first time, producing efficiently important anti β-hydroxy-α-amino acids. The total synthesis of several biologically active natural products was achieved by use of the transition metal-catalyzed reaction using DIAPHOX, anti-selective asymmetric hydrogenation, and reactions developed by us. Synthesis of tangutorine, an antitumor indole alkaloid, has been enantioselectively achieved for the first time. Enantioselective synthesis of a martinelline chiral core was accomplished using the asymmetric tandem Michael-Aldol reaction as a key step developed by us. This synthesis represents the formal total synthesis of martinelline and martinellic acid. Papuamide B was synthesized through the elucidation of unknown stereostructures by using the anti-selective asymmetric hydrogenation and reactions developed by us.

show abstract