250039-52-2

Upstream product

• 126587-61-9 Z-leucylprolyl-N,O-dimethyltyrosine-O-Boc-threonine-OSEM 

Downstream Products

• 325687-70-5 C₆₆H₁₀₉N₅O₁₆Si₂ 
• 250039-54-4 C₆₇H₁₁₁N₅O₁₆Si₂ 
• 250039-55-5 C₅₃H₈₉N₅SiO₁₂ 
• 250211-78-0 (-)-tamandarin A 
• 345664-76-8 4-amino-5-methyl-3-triisopropylsilanyloxy-heptanoic acid 1-[1-(2-{[1-(2-tert-butoxycarbonylamino-2-carboxy-1-methyl-ethoxycarbonyl)-2-(4-methoxy-phenyl)-ethyl]-methyl-carbamoyl}-pyrrolidine-1-carbonyl)-3-methyl-butylcarbamoyl]-2-methyl-propyl ester 
• 345664-75-7 C₆₁H₉₇N₅O₁₅Si 
• 258339-38-7 (-)-tamandarin B 
• 779313-73-4 (5S,8S,12S,13R,16S,17R,20S,22aS)-16-Amino-13-((S)-sec-butyl)-12-hydroxy-5-isobutyl-8-isopropyl-20-(4-methoxy-benzyl)-17,21-dimethyl-tetradecahydro-9,18-dioxa-3a,6,14,21-tetraaza-cyclopentacyclohenicosene-4,7,10,15,19,22-hexaone 
• 1053247-83-8 4-amino-5-methyl-3-triisopropylsilanyloxy-hexanoic acid 1-[1-(2-{[1-(2-tert-butoxycarbonylamino-2-carboxy-1-methyl-ethoxycarbonyl)-2-(4-methoxy-phenyl)-ethyl]-methyl-carbamoyl}-pyrrolidine-1-carbonyl)-3-methyl-butylcarbamoyl]-2-methyl-propyl ester 
• 345664-71-3 N-Z-prolyl-[Hiv²] didemnin A 
• 325687-71-6 [5-isobutyl-8,13-diisopropyl-20-(4-methoxy-benzyl)-17,21-dimethyl-4,7,10,15,19,22-hexaoxo-12-triisopropylsilanyloxy-eicosahydro-9,18-dioxa-3a,6,14,21-tetraaza-cyclopentacycloheneicosen-16-yl]-carbamic acid tert-butyl ester 

Relevant academic research and scientific papers

The first total synthesis of (-)-tamandarin A.

[formula: see text] Tamandarin A (1), a newly isolated natural product similar in structure to didemnin B (2), was shown to be somewhat more active in vitro than 2 against pancreatic carcinoma with an ED50 value 1.5 to 2 ng/mL. We report here the first total synthesis of 1. The key steps include a practical stereoselective synthesis of the Hiv-isostatine unit, high-yielding linear precursor formation, a successful macrocyclization, and coupling of the macrocycle with the side chain to afford tamandarin A (1).

Total syntheses and biological investigations of tamandarins A and B and tamandarin A analog

Tamandarins A (1) and B (2), two natural products similar in structure to didemnin B (3), were recently isolated from a Brazilian marine ascidian of the family Didemnidae. The cytotoxicity of 1 was reported to be somewhat more potent in vitro than that of 3 against various human cancer cell lines. The present account describes the first total syntheses of 1 and 2, and the syntheses of tamandarin A side chain analogues. The cytotoxicity data for these compounds show that the side chain modifications exhibit a parallel effect for both didemnins and tamandarins. This observation supports tamandarins' role as didemnins' mimic.

Total synthesis of (-)-tamandarin B

The synthesis of tamandarin B is described. Key steps in the synthesis of the macrocycle component include a diastereoselective ketone reduction, linear precursor formation via an activated pentafluorophenyl ester, and HATU-promoted cyclization. Side-chain coupling was achieved in excellent yield with the newly developed coupling reagent DEPBT. (C) 2000 Published by Elsevier Science Ltd.