Synthesis of Blastidic Acid and Cytosinine, Two Components of Blasticidin S

Ichikawa, Yoshiyasu; Ohbayashi, Masayoshi; Hirata, Keiko; Nishizawa, Rena; Isobe, Mitsuaki

doi:10.1055/s-2001-18108

Cited by 17 publications

(7 citation statements)

References 6 publications

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“…Cleavage of the 1,2-isopropylidene group of 148, followed by acetylation, led to the diacetate 149. Reaction of the silylated benzoyl adenine [38]. Blasticidin S is isolated from Streptomyces griseochromogenes and used as a fungicide for the prevention of rice blast in Japan.…”

Section: 13mentioning

confidence: 99%

“…Although of less biological importance than their openchain analogs, some cyclic hydroxylated -amino acid derivatives -where the amino and carboxylic functions are in neighboring ( ) positions on the alicyclic or heterocyclic ring -have antibiotic (oryzoxymycin) [27][28][29][30] or antifungal activities [31,32], and are building blocks for pharmaceutically important natural substances such as fortamine [33,34], chryscandin [35], pentopyranamine [36], gougerotin [37] and blasticidin [38].…”

Section: Introductionmentioning

confidence: 99%

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Syntheses of Hydroxylated Cyclic β-Amino Acid Derivatives

Palkó

Kiss²,

Fülöp

2005

CMC

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This review is intended to give a short summary of the developments in the field of natural and synthetic alicyclic and heterocyclic hydroxylated beta-amino acids and to focus on the main strategies that have been reported for their synthesis. Given the medicinal and biological significance of the hydroxylated beta-amino acids, an increasing volume of research is currently being directed toward regio-, stereo- and enantioselective access to this class of compounds.

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Section: 13mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Syntheses of Hydroxylated Cyclic β-Amino Acid Derivatives

Palkó

Kiss²,

Fülöp

2005

CMC

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“…This rearrangement was also used by Ichikawa for the synthesis of blasticidin S (Scheme ) . Dehydration of carbamate 42 , obtained from glucal 41 , led to isocyanate 43 .…”

Section: Applications In Natural Products Synthesismentioning

confidence: 99%

The Allyl Cyanate/Isocyanate Rearrangement: An Efficient Tool for the Stereocontrolled Formation of Allylic C–N Bonds

et al. 2017

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[3,3]‐Sigmatropic rearrangements represent powerful methods in the toolbox of synthetic organic chemists for the stereoselective construction of carbon–carbon as well as carbon–heteroatom bonds. Thus, the allyl cyanate/isocyanate rearrangement, although still underused for the preparation of allylamine derivatives, offers clear advantages over other similar methods. It usually occurs at or below ambient temperature with no need to use any metal catalyst, in a stereospecific way, and with a complete transfer of chirality. Moreover, combined with the high reactivity of the resulting isocyanates towards nucleophiles, this rearrangement gives access to various classes of compounds with wide structural and functional diversity. This microreview provides an overview of synthetic applications of this rearrangement since its discovery, with particular emphasis on its utility for the synthesis of complex nitrogen‐containing molecules such as natural products.

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“…In recent years, acyclic hydroxylated β -amino acids have attracted much attention especially following their recognition as an important class of compounds in the design and synthesis of potential pharmaceutical drugs [e.g., Taxol® (paclitaxel) and its analogue Taxotère® (docetaxel)] [ 17 , 19 , 20 , 21 ]. Among the carbocyclic β-amino acids a number of hydroxylated β-amino acid derivatives present antibiotic (e.g., oryzoxymycin [ 22 ]) or antifungal activity, and are building blocks for pharmaceutically important natural substances such as fortamine, chryscandin, pentopyranamine, gougerotin and blasticidin [ 20 , 23 ].…”

Section: Introductionmentioning

confidence: 99%