345664-75-7

Upstream product

• 250039-48-6 (2R,3S)-2-Benzyloxycarbonylamino-3-methyl-pentanoic acid pentafluorophenyl ester 
• 72-18-4 L-valine 
• 250039-53-3 (3S,4R,5S)-4-Benzyloxycarbonylamino-5-methyl-3-triisopropylsilanyloxy-heptanoic acid (S)-2-methyl-1-pentafluorophenyloxycarbonyl-propyl ester 
• 250039-51-1 (3S,4R,5S)-4-Benzyloxycarbonylamino-5-methyl-3-triisopropylsilanyloxy-heptanoic acid (S)-1-allyloxycarbonyl-2-methyl-propyl ester 
• 250039-47-5 (3S,4R,5S)-4-Benzyloxycarbonylamino-5-methyl-3-triisopropylsilanyloxy-heptanoic acid (S)-1-carboxy-2-methyl-propyl ester 
• 250039-50-0 (3S,4R,5S)-4-benzyloxycarbonylamino-5-methyl-3-(triisopropylsilanyloxy) heptanoic acid 
• 250039-49-7 (3S,4R,5S)-4-benzyloxycarbonylamino-5-methyl-3-(triisopropylsilanyloxy) heptanoic acid methyl ester 
• 250039-52-2 L-leucyl-L-prolyl-N,O-dimethyl-L-tyrosine-N-boc-O-SEM-L-threonine 
• 178113-56-9 L-2-hydroxy-3-methylbutanoic acid allyl ester 
• 126587-61-9 Z-leucylprolyl-N,O-dimethyltyrosine-O-Boc-threonine-OSEM 
• 17407-55-5 (S)-2-Hydroxy-3-methylbutanoic acid 
• 250039-54-4 C₆₇H₁₁₁N₅O₁₆Si₂ 
• 159360-04-0 (4R,5S)-4-benzyloxycarbonylamino-5-methyl-3-oxo-heptanoic acid methyl ester 
• 159407-39-3 (3S,4R,5S)-4-benzyloxycarbonylamino-3-hydroxy-5-methyl-heptanoic acid methyl ester 

Downstream Products

• 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 
• 250039-55-5 C₅₃H₈₉N₅SiO₁₂ 
• 250211-78-0 (-)-tamandarin A 
• 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 
• 345664-71-3 N-Z-prolyl-[Hiv²] didemnin A 

Relevant academic research and scientific papers

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.

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).