A total synthesis of indospicine, 6-Amidino-2-aminohexanoic acid

1971 ◽  
Vol 24 (2) ◽  
pp. 371 ◽  
Author(s):  
CCJ Culvenor ◽  
MC Foster ◽  
MPW Hegarty
Keyword(s):  
Amino Acid ◽  
Total Synthesis ◽  
Indigofera Spicata

Indospicine (1), the hepatotoxic amino acid from Indigofera spicata Forsk. is synthesized from 2-amino-6-hydroxyhexanoic acid (6- hydroxynorleucine) by stepwise replacement of hydroxyl by tosyloxy, cyano, imidoester, and amidine groupings.

Total synthesis of the antibiotic sparsomycin, a modified uracil amino acid monoxodithioacetal

1981 ◽  
Vol 46 (16) ◽  
pp. 3273-3283 ◽  
Author(s):  
Harry C. J. Ottenheijm ◽  
Rob M. J. Liskamp ◽  
Simon P. J. M. Van Nispen ◽  
Hans A. Boots ◽  
Marian W. Tijhuis
Keyword(s):  
Amino Acid ◽  
Total Synthesis

Studies Directed Towards the Total Synthesis of Anticapsin. X-Ray Crystal-Structure of (1RS,2SR,4RS,5RS,6SR)-5-Hydroxy-2-phthalimido-1-trimethylsilyloxy-bicyclo[2.2.2]octane-2,6-carbolactone

1990 ◽  
Vol 43 (11) ◽  
pp. 1827 ◽  
Author(s):  
MJ Crossley ◽  
TW Hambley ◽  
AW Stamford
Keyword(s):  
Crystal Structure ◽  
Amino Acid ◽  
Total Synthesis ◽  
Synthetic Approach ◽  
Hydrogen Atoms ◽  
Full Matrix ◽  
X Ray ◽  
X Ray Crystallography ◽  
Relative Stereochemistry ◽  
Atomic Parameters

The relative stereochemistry of methyl 2-phthalimido-1- trimethylsilyloxybicyclo[2.2.2]oct-5-ene-2-carboxylate (9) and its 5,6-epoxide (10), intermediates in a synthetic approach to the amino acid antibiotic anticapsin, were established by the TiCl4-mediated cyclization of (10) to the carbolactone (12); the structure of which was proved by single-crystal X-ray crystallography. Full-matrix least- squares refinement of all atomic parameters with individual isotropic thermal parameters for the hydrogen atoms by using 1446 reflections converged at R 0.036. Crystals of (12) are monoclinic, P21/c, a 12.342(3), b 12.239(2), c 13.405(3) Ǻ, β 99.34(2)°, Z 4.

scholarly journals A Reliable Enantioselective Route to Mono-Protected N1-Cbz Piperazic Acid Building Block

Molecules ◽  
2020 ◽  
Vol 25 (24) ◽  
pp. 5939
Author(s):  
Evanthia Papadaki ◽  
Dimitris Georgiadis ◽  
Michail Tsakos
Keyword(s):  
Natural Products ◽  
Amino Acid ◽  
Total Synthesis ◽  
Building Block ◽  
Optical Purity ◽  
Protecting Group ◽  
High Optical Purity

The chiral N1-Cbz, N2-H derivative of the piperazic acid monomer is a valuable building block in the total synthesis of natural products, comprising this nonproteinogenic amino acid. In that context, we wish to report an improved synthetic protocol for the synthesis of both (3R)- and (3S)-piperazic acids bearing the carboxybenzyl protecting group (Cbz) selectively at the N1 position. Our method builds on previously reported protocols, circumventing their potential shortcomings, and optimizing the ultimate selective deprotection at the N2 position, thus, offering an efficient and reproducible pathway to suitably modified piperazates in high optical purity.

Total Synthesis of Azumamide E and Sugar Amino Acid-Containing Analogue

2009 ◽  
Vol 74 (1) ◽  
pp. 401-404 ◽  
Author(s):  
Srivari Chandrasekhar ◽  
Chennamaneni Lohitha Rao ◽  
Mallikanti Seenaiah ◽  
Police Naresh ◽  
Bharatam Jagadeesh ◽  
...  
Keyword(s):  
Amino Acid ◽  
Total Synthesis

Diastereoselective total synthesis of (+)-morusimic acid B, an amino acid from Morus alba

Tetrahedron ◽  
2007 ◽  
Vol 63 (12) ◽  
pp. 2712-2723 ◽  
Author(s):  
Marc E. Bouillon ◽  
Hartmut H. Meyer
Keyword(s):  
Amino Acid ◽  
Total Synthesis ◽  
Morus Alba
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