A new, versatile and stereospecific route to unusual amino acids: the enantiospecific total synthesis of statine amide and its three stereoisomers

1992 ◽  
Vol 57 (16) ◽  
pp. 4441-4444 ◽  
Author(s):  
M. Bessodes ◽  
M. Saiah ◽  
K. Antonakis
Synthesis ◽  
2018 ◽  
Vol 51 (01) ◽  
pp. 107-121 ◽  
Author(s):  
Alexander Kiefer ◽  
Uli Kazmaier

The cyclomarins are cyclic heptapeptides from marine streptomycetes containing four rather unusual amino acids. Interestingly, the cyclomarins address two completely different targets: ClpC1, a subunit of the caseinolytic protease of Mycobacterium tuberculosis (MTB), as well as PfAp3Aase of Plasmodium falciparum. Therefore, the cyclomarins are interesting lead structures for the development of drugs targeting tuberculosis and malaria. As a result, several synthetic protocols towards the synthesis of these unusual building blocks as well as the natural products themselves have been developed, which will be discussed in this review.1 Introduction2 Synthesis of the Building Blocks3 Total Synthesis of Cyclomarin C by Yao and Co-workers4 Total Synthesis of Cyclomarin A and C by Barbie and Kazmaier5 Conclusion


Synlett ◽  
2018 ◽  
Vol 29 (18) ◽  
pp. 2342-2361 ◽  
Author(s):  
Sambasivarao Kotha ◽  
Kakali Lahiri ◽  
Gaddamedi Sreevani

The [2+2+2] cycloaddition reaction is a useful tool to realize unusual chemical transformations which are not achievable by traditional methods. Here, we report our work during the past two decades that involve utilization of transition-metal complexes in a [2+2+2] cyclotrimerization reaction. Several key “building blocks” were assembled by a [2+2+2] cycloaddition approach and they have been further expanded by other synthetic transformations to design unusual amino acids and peptides, diphenylalkanes, bis- and trisaryl benzene derivatives, annulated benzocycloalkanes, spirocycles, and spirooxindole derivatives. Furthermore, we have also discussed about alkyne surrogates, environmentally friendly, and stereoselective [2+2+2] cycloaddition reactions. Application of the [2+2+2] cycloaddition reaction in total synthesis is also covered. In this review we also included others work to give a balanced view of the recent developments in the area of [2+2+2] cycloaddition.1 Introduction2 Unusual Amino Acids and Peptides3 Heteroanalogues of Indane4 Diphenylalkane Derivatives5 Multi-Armed Aryl Benzene Derivatives6 Annulated Benzocycloalkanes7 Spirocycles8 Selectivity in [2+2+2] Cycloaddition of Alkynes9 [2+2+2] Cycloaddition Reactions under Environmentally Friendly Conditions10 Alkyne Surrogates11 Domino Reactions involving a [2+2+2] Cycloaddition12 Biologically Important Targets/Total Synthesis13 Conclusions


2016 ◽  
Vol 14 (25) ◽  
pp. 6036-6054 ◽  
Author(s):  
Philipp Barbie ◽  
Uli Kazmaier

Cyclomarins are cyclic heptapeptides containing four unusual amino acids.


2002 ◽  
Vol 74 (1) ◽  
pp. 159-166 ◽  
Author(s):  
Iwao Ojima

Recent development in the transition metal-catalyzed cyclization reactions for organic syntheses in the author's laboratories is summarized, which includes (i) novel silylcarbocyclizations (SiCaCs) and carbonylative carbotricyclizations, (ii) intramolecular silylformylations and desymmerization of siloxydiynes by sequential double silylformylation, (iii) efficient total synthesis of (+)-prosopinine, (iv) enantioselective desymmetrization of aminodienes, and (iv) new and efficient routes to 1-azabicyclo[x.y.0]alkane amino acids. All these processes are catalyzed by Rh or Rh­Co complexes, and useful for rapid and efficient construction of a variety of heterocyclic and carbocyclic compounds. Mechanisms of these new carbocyclization and cyclohydrocarbonylation reactions are also discussed.


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