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
2019 ◽  
Vol 15 ◽  
pp. 577-583 ◽  
Author(s):  
Jan Hendrik Lang ◽  
Thomas Lindel

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.


Author(s):  
François Morvan ◽  
Aude-Emmanuelle Navarro ◽  
Cécile Dueymes ◽  
Ilaria Adamo ◽  
Andreas Schoenberger ◽  
...  

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

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

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