A Flexible Common Approach to α‐Substituted Serines and Alanines: Diastereoconvergent Syntheses of Sphingofungins E and F

Wang, Bing; Lin, Guo‐Qiang

doi:10.1002/ejoc.200900772

“…It exhibits inhibitory effects toward serine palmitoyl transferase (SPT), which induces apoptosis in both yeast and mammalian cells by blocking the sphingosine biosynthesis pathway . Due to its structural novelty and biological activity, the synthesis of sphingofungin F has attracted considerable attention to synthetic chemists . The first asymmetric synthesis of sphingofugin F was achieved by Kobayashi using Sn II -catalyzed asymmetric aldol reaction of Schöllkopf’s bislactam in 1997 with 6.5% overall yield in 24 steps .…”

mentioning

confidence: 99%

Total Synthesis of Sphingofungin F Based on Chiral Tricyclic Iminolactone

Gan

¹

,

Yang

²

,

Luo

³

et al. 2010

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A new, efficient synthesis of sphingofungin F has been accomplished with 10.4% overall yield in 15 steps. The salient features of the synthesis are the utilization of methyl tricyclic iminolactone 3 for the asymmetric aldol reaction as a key step to introduce two desired stereogenic centers, one-pot reaction for the synthesis of omega-hydroxyketone from epsilon-caprolactone, and an effective one-step deprotection strategy to remove all protecting groups using 0.2 N HCl.

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“…Due to their intriguing structural features and important pharmacological properties, sphingofungins became quickly popular total synthetic targets. Until today, 14 distinct synthetic strategies have been applied in the total synthesis of sphingofungins B, D, E, and F,[ 12 , 13 , 14 , 15 , 16 , 17 , 18 , 19 , 20 , 21 , 22 , 23 , 24 , 25 , 26 , 27 , 28 , 29 , 30 , 31 , 32 , 33 , 34 , 35 , 36 ] with the last syntheses of sphingofungin E and F being reported in 2017 by Noda et al. [35] and Sugai et al.…”

Section: Introductionmentioning

confidence: 99%

A Modular Approach to the Antifungal Sphingofungin Family: Concise Total Synthesis of Sphingofungin A and C

Raguž

¹

,

Peng

²

,

Kaiser

³

et al. 2021

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Sphingofungins are fungal natural products known to inhibit the biosynthesis of sphingolipids which play pivotal roles in various cell functions.H ere,w er eport as hort and flexible synthetic approach towards the sphingofungin family. Keystep of the synthesis was adecarboxylative cross-coupling reaction of chiral sulfinyl imines with afunctionalizedtartaric acid derivative,whichyielded the core motif of sphingofungins carrying four consecutive stereocenters and at erminal double bond. Subsequent metathesis reaction allowed for the introduction of different side chains of choice resulting in atotal of eight sphingofungins,i ncluding for the first time sphingofungin C( eight steps from commercially available protected tartaric acid with an overall yield of 6%)and sphingofungin A (ten steps). All newly synthesized derivatives were tested for their antifungal, cell-proliferative and antiparasitic activity unraveling their structure-activity relations.

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“…Due to their intriguing structural features and important pharmacological properties, sphingofungins became quickly popular total synthetic targets. Until today, 14 distinct synthetic strategies have been applied in the total synthesis of sphingofungins B, D, E, and F, [12–36] with the last syntheses of sphingofungin E and F being reported in 2017 by Noda et al [35] . and Sugai et al [36] .…”

Section: Introductionmentioning

confidence: 99%

A Modular Approach to the Antifungal Sphingofungin Family: Concise Total Synthesis of Sphingofungin A and C

Raguž

¹

,

Peng

²

,

Kaiser

³

et al. 2021

Angewandte Chemie

2

0

View full text Add to dashboard Cite

Sphingofungins are fungal natural products known to inhibit the biosynthesis of sphingolipids which play pivotal roles in various cell functions.H ere,w er eport as hort and flexible synthetic approach towards the sphingofungin family. Keystep of the synthesis was adecarboxylative cross-coupling reaction of chiral sulfinyl imines with afunctionalizedtartaric acid derivative,whichyielded the core motif of sphingofungins carrying four consecutive stereocenters and at erminal double bond. Subsequent metathesis reaction allowed for the introduction of different side chains of choice resulting in atotal of eight sphingofungins,i ncluding for the first time sphingofungin C( eight steps from commercially available protected tartaric acid with an overall yield of 6%)and sphingofungin A (ten steps). All newly synthesized derivatives were tested for their antifungal, cell-proliferative and antiparasitic activity unraveling their structure-activity relations.

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A Flexible Common Approach to α‐Substituted Serines and Alanines: Diastereoconvergent Syntheses of Sphingofungins E and F

Cited by 25 publications

References 70 publications

Total Synthesis of Sphingofungin F Based on Chiral Tricyclic Iminolactone

Total Synthesis of Sphingofungin F Based on Chiral Tricyclic Iminolactone

A Modular Approach to the Antifungal Sphingofungin Family: Concise Total Synthesis of Sphingofungin A and C

A Modular Approach to the Antifungal Sphingofungin Family: Concise Total Synthesis of Sphingofungin A and C

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