ChemInform Abstract: A New and Convenient Method for the Synthesis of Dehydroamino Acids Starting from Ethyl N‐Boc‐ and N‐Z‐α‐Tosylglycinates and Various Nitro Compounds.

Nagano, Tanemasa; Kinoshita, Hideki

doi:10.1002/chin.200041057

Cited by 3 publications

(3 citation statements)

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“…On the other hand, the corresponding N -Boc imine 7c possesses suitable stability and reactivity, but it is difficult to isolate it. Thus, it was generated in situ from the corresponding sulfonyl precursor 9 43 with DBU. A domino reaction of 8 and 9 , involving the generation of the imine and the aza-Henry reaction, proceeded well to afford piperidine 4 and tetrahydropyridine 10 in 35% and 50% yield, respectively (Fig.…”

Section: Resultsmentioning

confidence: 99%

Organocatalyst-mediated five-pot synthesis of (–)-quinine

Terunuma

Hayashi

2022

Nat Commun

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In this work, the enantioselective total synthesis of (–)-quinine has been accomplished in a pot-economical manner using five reaction vessels. In the first pot, reactions involve the diphenylprolinol silyl ether-mediated Michael reaction, aza-Henry reaction, hemiaminalization, and elimination of HNO2 (five reactions), affording a chiral tetrahydropyridine with excellent enantioselectivity. In the second pot, five reactions proceed with excellent diastereoselectivity to afford a trisubstituted piperidine with the desired stereochemistry. A further five reactions are carried out in the last one-pot sequence.

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Section: Resultsmentioning

confidence: 99%

Organocatalyst-mediated five-pot synthesis of (–)-quinine

Terunuma

Hayashi

2022

Nat Commun

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“…Nagano et al reported an approach for obtaining dehydroamino acids 63 starting from alpha-tosyl glycine 62 and various nitroalkene in the presence of DBU as a base ( Figure 23 ) [ 83 ].…”

Section: Chemical Synthesismentioning

confidence: 99%

Thirtieth Anniversary of the Discovery of Laxaphycins. Intriguing Peptides Keeping a Part of Their Mystery

et al. 2021

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Lipopeptides are a class of compounds generally produced by microorganisms through hybrid biosynthetic pathways involving non-ribosomal peptide synthase and a polyketyl synthase. Cyanobacterial-produced laxaphycins are examples of this family of compounds that have expanded over the past three decades. These compounds benefit from technological advances helping in their synthesis and characterization, as well as in deciphering their biosynthesis. The present article attempts to summarize most of the articles that have been published on laxaphycins. The current knowledge on the ecological role of these complex sets of compounds will also be examined.

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“…Many methods available for synthesis of α,β-dehydroamino acids have been reported (Bonauer et al 2006 ; Poisel and Schmidt 1976 ; Kolasa 1983 ; Maekawa et al 2004 ; Schmidt et al 1992 ; Trost and Dake 1997 ; Nagano and Kinoshita 2000 ; Chen et al 2005 ; Goodall and Parsons 1995 ; Li et al 1996 ; Somekh and Shanzer 1983 ; Miller 1980 ; Stohimeyer et al 1999 ). However, these methods often are low yielding, multistep, require tedious purification steps to remove reagent side products, or incorporate unusual, difficultly obtained amino acid intermediates.…”

Section: Introductionmentioning

confidence: 99%

Stereoselectively synthesis and structural confirmation of dehydrodipeptides with dehydrobutyrine

Xia

Han

et al. 2016

SpringerPlus

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Most of polypeptides containing α,β-dehydroamino acids have important biological activity, so exploration of synthetic method has practical significance. In this paper, dipeptides were prepared from l-threonine by protecting of c-terminal allyl acetate, and condensing reaction with a series of N-Boc amino acid. Then, treatment of dipeptides obtained with DMAP, (Boc)2O and tetramethylguanidine in the acetonitrile occured β-elimination reaction to yield stereoselectively dehydrodipeptides. Structures of dehydrodipeptides were confirmed by 1H NMR, 13C NMR and MS. Analysis of 1H NMR, 2D NMR and crystal structure showed that the dehydrodipeptides were Z-configuration.Graphical abstractDehydrodipeptides were prepared from l-threonine. Their structures were confirmed by 1H NMR, 13C NMR and MSElectronic supplementary materialThe online version of this article (doi:10.1186/s40064-016-2005-z) contains supplementary material, which is available to authorized users.

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ChemInform Abstract: A New and Convenient Method for the Synthesis of Dehydroamino Acids Starting from Ethyl N‐Boc‐ and N‐Z‐α‐Tosylglycinates and Various Nitro Compounds.

Cited by 3 publications

References 1 publication

Organocatalyst-mediated five-pot synthesis of (–)-quinine

Organocatalyst-mediated five-pot synthesis of (–)-quinine

Thirtieth Anniversary of the Discovery of Laxaphycins. Intriguing Peptides Keeping a Part of Their Mystery

Stereoselectively synthesis and structural confirmation of dehydrodipeptides with dehydrobutyrine

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