Total synthesis of the indole alkaloids henrycinol A and B

Prasad, Kavirayani R.; Nidhiry, John Eugene; Sridharan, Makuteswaran

doi:10.1016/j.tet.2014.05.028

Cited by 5 publications

(5 citation statements)

References 20 publications

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“…184 The Prasad group also accomplished the total syntheses of henrycinols A and B by the reaction of L-tryptophan methyl ester with an enantioenriched aldehyde derived from 2,3-O-isopropylidene-Dthreitol. 185 Following the same blueprint, Stork and co-workers reported in 2005 the asymmetric preparation of a classic synthesis target, the indole alkaloid reserpine (Scheme 38). 186 The challenging Picket−Spengler cyclization was addressed on the basis of the assumption that the kinetic mode of cyclization of an iminium ion generated regioselectively would lead to the formation of the desired, thermodynamically less stable diastereomer 38-6.…”

Section: Chemical Reviewsmentioning

confidence: 99%

“…Prasad and Nidhiry utilized a reaction between tryptamine 37 - 4 and aldehyde 37 - 5 for the enantioselective synthesis of eburnamonine; however, application of trifluoroacetic acid in CH 2 Cl 2 at −20 °C for the Picket–Spengler reaction resulted in the production of 37 - 6 with low diastereoselectivity (3:2) (Scheme b) . The Prasad group also accomplished the total syntheses of henrycinols A and B by the reaction of l -tryptophan methyl ester with an enantioenriched aldehyde derived from 2,3- O -isopropylidene- d -threitol …”

Section: Addition To the Carbon–nitrogen Double Bondmentioning

confidence: 99%

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Cutting-Edge and Time-Honored Strategies for Stereoselective Construction of C–N Bonds in Total Synthesis

et al. 2016

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The main objective of this review is to provide a comprehensive survey of methods used for stereoselective construction of carbon-nitrogen bonds during the total synthesis of nitrogen-containing natural products that have appeared in the literature since 2000. The material is organized by specific reaction in order of decreasing number of applications in natural product synthesis. About 800 total syntheses of natural products with stereogenic carbon-nitrogen bonds described since 2000 have been reviewed.

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Section: Chemical Reviewsmentioning

confidence: 99%

Section: Addition To the Carbon–nitrogen Double Bondmentioning

confidence: 99%

Cutting-Edge and Time-Honored Strategies for Stereoselective Construction of C–N Bonds in Total Synthesis

et al. 2016

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“…In 2014, Prasad et al. synthesized these alkaloids using highly diastereoselective Pictet‐Spengler and post‐Pictet‐Spengler Cyclization reaction as key steps (Scheme ) . The Pictet‐Spengler reaction of N ‐allyl‐ L ‐tryptophan methyl ester 250 with the aldehyde, afforded the 1,3‐ trans ‐1,2,3,4‐tetrahydro‐β‐carboline 251 as the major product in 84% yield.…”

Section: β‐Carboline Fused Heterocycles Synthesized Via Post Pictet‐smentioning

confidence: 99%

Post‐Pictet‐Spengler Cyclization (PPSC): A Strategy to Synthesize Polycyclic β‐Carboline‐Derived Natural Products and Biologically Active N‐Heterocycles

Singh

Kumar

Patil³

et al. 2020

Adv Synth Catal

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Pictet-Spengler reaction is a typical condensation reaction of β-arylethylamine or Tryptamine with an aldehyde or ketone followed by ring closure to generate tetrahydroisoquinoline (THIQ) and Tetrahydro-β-carboline (THβC), respectively. Both these key skeletons represent huge range of structurally diverse naturally occurring isoquinoline and indole alkaloids. Nature has synthesized structurally complex Reserpine, Ajmalicine as well as other related alkaloids using various biosynthetic pathways via Pictet-Spengler reaction followed by post-Pictet-Spengler cyclization (PPSC) stratergy. This biosynthetic process is the short and reliable method to access diverse range of polycyclic heterocycles. Over the period of last sixty years, several researchers have synthesized complex alkaloids without highlighting the synthetic utility of the post-Pictet-Spengler cyclization strategy. We summarized the synthesis of numerous natural products and related natural product inspired heterocyclic scaffolds which follow the PPSC strategy to demonstrate its usefulness for the construction of diverse compound collection.

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“…Significantly, stereoselective first total synthesis of the indole alkaloids henrycinol A 71 and B 72 were performed from N -allyl- l -tryptophan methylester 68 and (−),2,3- O -isopropylidene- d -threitolin 34% and 8% overall yields, respectively in eight and nine linear stages. The key conversion was the trans -selective construction of 1,3-dialkyl-1,2,3,4-tetrahydro-β-carboline in the Pictet–Spengler cyclisation ( Scheme 14 ) [ 158 ].…”

Section: Pictet–spengler Reaction In the Total Synthesis Of Naturamentioning

confidence: 99%

Application of the Asymmetric Pictet–Spengler Reaction in the Total Synthesis of Natural Products and Relevant Biologically Active Compounds

2018

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Tetrahydroisoquinolines are the framework of numerous natural products predominantly alkaloids, an important and one of the most wide spread families of naturally occurring compounds in the plant kingdom. Tetrahydroisoquinolines are commonly constructed through an old reaction, the so-called Pictet–Spengler Reaction (PSR). In this reaction, a β-aryl ethylamine undergoes an acid mediated condensation with a suitable aldehyde or ketone, followed by ring closure. In this review, we aim to highlight the applications of the asymmetric variant of this old name reaction in the total synthesis of natural products, chiefly, alkaloids, which exhibit significant biological properties.

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Total synthesis of the indole alkaloids henrycinol A and B

Cited by 5 publications

References 20 publications

Cutting-Edge and Time-Honored Strategies for Stereoselective Construction of C–N Bonds in Total Synthesis

Cutting-Edge and Time-Honored Strategies for Stereoselective Construction of C–N Bonds in Total Synthesis

Post‐Pictet‐Spengler Cyclization (PPSC): A Strategy to Synthesize Polycyclic β‐Carboline‐Derived Natural Products and Biologically Active N‐Heterocycles

Application of the Asymmetric Pictet–Spengler Reaction in the Total Synthesis of Natural Products and Relevant Biologically Active Compounds

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