scholarly journals Synthesis of the polyketide section of seragamide A and related cyclodepsipeptides via Negishi cross coupling

2019 ◽  
Vol 15 ◽  
pp. 577-583 ◽  
Author(s):  
Jan Hendrik Lang ◽  
Thomas Lindel
Keyword(s):  
Natural Products ◽  
Natural Product ◽  
Propylene Oxide ◽  
Cross Coupling ◽  
Solution Phase ◽  
Partial Structure ◽  
Open Chain ◽  
Phase Synthesis ◽  
Solution Phase Synthesis ◽  
Ester Enolate

The synthesis of the polyketide section present in the potently cytotoxic marine cyclodepsipeptide jasplakinolide and related natural products, geodiamolides and seragamides, is reported. The key step is a Negishi cross coupling of (R)-(3-methoxy-2-methyl-3-oxopropyl)zinc(II) bromide and an (E)-iodoalkene that was synthesized via an aluminium ester enolate attack at (R)-propylene oxide. The overall synthesis comprises nine steps with an overall yield of 21%. It proved to be possible to liberate the free 8-hydroxynonenoic acid and to couple it with a protected tripeptide composed of L-alanine, N,O-dimethyl-D-iodotyrosine, and TIPS-protected L-threonine, which occurs as partial structure of seragamide A. The tripeptide section of seragamide A was assembled by solution-phase synthesis and an open-chain analogue of the natural product was obtained.

Gram-Scale Solution-Phase Synthesis of Heptapeptide Side Chain of Teixobactin

Synlett ◽  
2019 ◽  
Vol 30 (20) ◽  
pp. 2268-2272 ◽  
Author(s):  
Sangeetha Donikela ◽  
Kiranmai Nayani ◽  
Vishnuvardhan Nomula ◽  
Prathama S. Mainkar ◽  
Srivari Chandrasekhar
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Natural Product ◽  
Solution Phase ◽  
Side Chain ◽  
Phase Synthesis ◽  
Solution Phase Synthesis ◽  
Efficient Coupling ◽  
Scalable Synthesis

We report herein a scalable synthesis of linear heptapeptide side chain of the depsipeptide natural product teixobactin through solution phase. The synthesis of heptapeptide was achieved through an efficient coupling of suitably protected tripeptide and tetrapeptide comprising of three d-amino acids and four usual l-amino acid subunits.

Solution-Phase Synthesis of an Aminomethyl-Substituted Biaryl Library via Sequential Amine N-Alkylation and Suzuki Cross-Coupling

2001 ◽  
Vol 3 (5) ◽  
pp. 473-476 ◽  
Author(s):  
Michael G. Organ ◽  
Elena A. Arvanitis ◽  
Craig E. Dixon ◽  
David J. Lavorato
Keyword(s):  
Cross Coupling ◽  
Solution Phase ◽  
Phase Synthesis ◽  
Solution Phase Synthesis

Solution phase synthesis of oligonucleotides by the phosphoramidite method using solid supported reagents

2005 ◽  
Author(s):  
François Morvan ◽  
Aude-Emmanuelle Navarro ◽  
Cécile Dueymes ◽  
Ilaria Adamo ◽  
Andreas Schoenberger ◽  
...  
Keyword(s):  
Solution Phase ◽  
Phase Synthesis ◽  
Solution Phase Synthesis

Polymer-Assisted Parallel Solution Phase Synthesis of Substituted Benzimidazoles.

ChemInform ◽  
2010 ◽  
Vol 33 (35) ◽  
pp. 123-123
Author(s):  
Young K. Yun ◽  
John A. Porco Jr. ◽  
Jeff Labadie
Keyword(s):  
Solution Phase ◽  
Phase Synthesis ◽  
Parallel Solution ◽  
Solution Phase Synthesis
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