Solution Phase Synthesis of Libraries of Polycyclic Natural Product Analogues by Cascade Radical Annulation:  Synthesis of a 64-Member Library of Mappicine Analogues and a 48-Member Library of Mappicine Ketone Analogues

2000 ◽  
Vol 2 (6) ◽  
pp. 639-649 ◽  
Author(s):  
Oscar de Frutos ◽  
Dennis P. Curran
Keyword(s):  
Natural Product ◽  
Solution Phase ◽  
Phase Synthesis ◽  
Solution Phase Synthesis

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.

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.

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

Solution-phase synthesis of monodispersed SnTe nanocrystallites at room temperature

2003 ◽  
Vol 6 (2) ◽  
pp. 181-184 ◽  
Author(s):  
Changhua An ◽  
Kaibin Tang ◽  
Bin Hai ◽  
Guozhen Shen ◽  
Chunrui Wang ◽  
...  
Keyword(s):  
Room Temperature ◽  
Solution Phase ◽  
Phase Synthesis ◽  
Solution Phase Synthesis

Synthesis of O-Phosphotyrosine-Containing Peptides. II. Solution-Phase Synthesis of Asn-Glu-PTyr-Thr-Ala Through Methyl Phosphate Protection

1989 ◽  
Vol 42 (9) ◽  
pp. 1519 ◽  
Author(s):  
RM Valerio ◽  
JW Perich ◽  
EA Kitas ◽  
PF Alewood ◽  
RB Johns
Keyword(s):  
Trifluoroacetic Acid ◽  
Dimethyl Sulfide ◽  
Solution Phase ◽  
High Yield ◽  
Phase Synthesis ◽  
Rous Sarcoma ◽  
Naturally Occurring ◽  
Solution Phase Synthesis ◽  
Sarcoma Virus ◽  
Methyl Phosphate

The PTyr (O-phosphotyrosine) pentapeptide H-Asn-Glu-Tyr(PO3H2)-Thr-Ala-OH.HO2CCF3, which is a naturally occurring sequence from the autophosphorylated Rous sarcoma virus pp60V-SrC, was prepared in high yield by the use of Boc-Tyr(PO3Me2)-OH in the Boc mode of solution-phase peptide synthesis. The protected pentapeptide, Z-Asn-Glu(OBzl)-Tyr(PO3Me2)-Thr(Bzl)-Ala-OBzl, was deprotected by a two-stage procedure which involved initial palladium-catalysed hydrogenolysis followed by the removal of the phosphate methyl groups by the use of one of the following treatments: (A) 10% bromotrimethylsilane/acetonitrile, (B) 1 M bromotrimethylsilane/thioanisole in trifluoroacetic acid, or (C) trifluoromethanesulfonic acid/trifluoroacetic acid/dimethyl sulfide/m-cresol.

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