219606-86-7

Upstream product

• 27784-76-5 tert-butyl diethylphosphonoacetate 
• 219606-82-3 (2S,2'R)-benzyl 2-[(3'-{[(tert-butoxy)carbonyl]amino}propionyl)oxy]-4-methylpentanoate 
• 245125-85-3 (S)-2-(3-Amino-propionyloxy)-4-methyl-pentanoic acid benzyl ester 
• 37755-48-9 benzyl (2S)-2-hydroxy-4-methylpentanoate 
• 219606-83-4 benzyl (2S)-2-[3-[(2R)-2-tert-butoxycarbonylamino-3-(4-methoxyphenyl)propionylamino]-propionyloxy]-4-methylpentanoate 
• 219606-75-4 tert-butyl (5S,6R)-5-tert-butyldimethylsilanyloxy-7-(4-methoxybenzyloxy)-6-methylhept-2(E)-enoate 
• 219606-74-3 (3S,4R)-3-tert-butyldimethylsilanyloxy-5-(4-methoxybenzyloxy)-4-methylpentanal 
• 219606-73-2 tert-Butyl-{(S)-1-[(R)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-but-3-enyloxy}-dimethyl-silane 
• 219606-78-7 tert-butyl (5S,6R)-5-tert-butyldimethylsilanyloxy-8-iodo-6-methylocta-2(E),7(E)-dienoate 
• 219606-76-5 tert-butyl (5S,6R)-5-tert-butyldimethylsilanyloxy-7-hydroxy-6-methylhept-2(E)-enoate 
• 219606-77-6 tert-butyl (5S,6S)-5-tert-butyldimethylsilanyloxy-6-methyl-7-oxohept-2(E)-enoate 
• 219606-81-2 (3R,4S)-4,6-bis(tert-butyldimethylsilyloxy)-3-methylhex-1-ene 
• 203926-55-0 (2R,3S)-1-[(4-methoxyphenyl)methoxy]-2-methyl-5-hexen-3-ol 
• 168777-81-9 (3S,4R)-1-[(tert-butyldimethylsilyl)oxy]-4-methylhex-5-en-3-ol 

Downstream Products

• 162473-78-1 desepoxyarenastatin A 
• 162600-54-6 cryptophycin-24 
• 162600-54-6 cryptophycin-24 
• 162600-54-6 arenastatin A 
• 162600-54-6 arenastatin A 
• 162600-54-6 (E)-(3S,10R,16S)-3-Isobutyl-10-(4-methoxy-benzyl)-16-[(S)-1-((2S,3R)-3-phenyl-oxiranyl)-ethyl]-1,4-dioxa-8,11-diaza-cyclohexadec-13-ene-2,5,9,12-tetraone 

Relevant academic research and scientific papers

Total synthesis of cryptophycin-24 (arenastatin A) amenable to structural modifications in the C16 side chain

Two efficient protocols for the synthesis of tert-butyl (5S,6R,2E,7E)-5-[(tert-butyldimethylsilyl)-oxy]-6-methyl-8-phenyl-2,7-octadie noate, a major component of the cryptophycins, are reported. The first utilized the Noyori reduction and Frater alkylation of methyl 5-benzyloxy-3-oxopentanoate to set two stereogenic centers, which became the C16 hydroxyl and C1' methyl of the cryptophycins. The second approach started from 3-p-methoxybenzyloxypropanal and a crotyl borane reagent derived from (-)-α-pinene to set both stereocenters in a single step and provided the dephenyl analogue, tert-butyl (5S,6R,2E)-5-[(tert-butyldimethylsilyl)oxy]-6-methyl-2,7-octadienoate, in five steps. This compound was readily converted to the 8-phenyl compound via Heck coupling. The silanyloxy esters were efficiently deprotected and coupled to the C2-C10 amino acid fragment to provide desepoxyarenastatin A and its dephenyl analogue. The terminal olefin of the latter was further elaborated via Heck coupling. Epoxidation provided cryptophycin-24 (arenastatin A).

Total Synthesis of Cryptophycins-1, -3, -4, -24 (Arenastatin A), and -29, Cytotoxic Depsipeptides from Cyanobacteria of the Nostocaceae

A convergent synthesis of cryptophycins has been developed in which (5S,6R)-5-hydroxy-6-methyl-8-phenylocta-2(E),7(E)-dienoic acid (A) is coupled with an amino acid segment (B). Two stereo-selective routes to A are described, the first employing allylatio

A concise synthesis of the cytotoxic depsipeptide arenastatin A

Arenastatin A (1, cryptophycin 24) was synthesized by convergence of hydroxy ester 16 with amino acid derivative 27; two independent and highly efficient routes to 16 are disclosed.