1213264-72-2

Upstream product

• 1213265-02-1 (2S)-3,3-dimethyl-1,2-epoxy-4-(tetrahydropyran-2-yloxy)-butane 
• 104708-02-3 2-Methyl-2-(S)-oxiranyl-propan-1-ol 
• 1213264-68-6 (3R)-7-((4-methoxybenzyl)oxy)-2,2-dimethyl-1-((tetrahydro-2H-pyran-2-yl)oxy)hept-5-yn-3-ol 
• 1213264-70-0 (R)-3-hydroxy-7-((4-methoxybenzyl)oxy)-2,2-dimethylhept-5-ynal 
• 24850-33-7 allyltributylstanane 

Downstream Products

• 1213265-06-5 (4R,6R)-4,6-bistriethylsilyloxy-5,5-dimethyl-10-(4-methoxybenzyloxy)-1-decen-8-yne 
• 1213265-12-3 (4R,6R,8R,9R)-10-(benzyloxymethoxy)-4,6-bistriethylsilyloxy-5,5-dimethyl-8,9-epoxy-1-decene 
• 1213265-14-5 (2R,4R,6S)-2-allyl-6-((1R)-2-(benzyloxymethoxy)-1-hydroxyethyl)-3,3-dimethyl-4-hydroxytetrahydropyran 
• 1213264-76-6 (2R,4R,6S)-2-allyl-6-((1R)-2-(benzyloxymethoxy)-1-methoxyethyl)-3,3-dimethyl-4-hydroxytetrahydropyran 
• 1213265-17-8 (2R,4R,6S)-2-allyl-6-((1R)-2-(benzyloxymethoxy)-1-methoxyethyl)-3,3-dimethyl-4-tert-butyldimethylsilyloxytetrahydropyran 
• 1213264-80-2 (2R,4R,6S)-6-((1R)-2-(benzyloxymethoxy)-1-methoxyethyl)-3,3-dimethyl-2-(2-oxobutyl)-4-tert-butyldimethylsilyloxytetrahydropyran 
• 1213264-65-3 (2R,4R,6S)-6-((1S)-1-benzyloxycarbonyl-1-methoxymethyl)-3,3-dimethyl-2-(2-oxobutyl)-4-tert-butyldimethylsilyloxytetrahydropyran 
• 1213264-82-4 (S)-benzyl 2-((2S,4R,6R)-tetrahydro-5,5-dimethyl-6-((3S,4R)-4-hydroxy-3-methyl-5-(6-methyl-2-methyloxycarbonyl-3,5-bistriisopropylsilyloxyphenyl)-2-oxopentyl)-4-tert-butyldimethylsilyloxy-2H-pyran-2-yl)-2-methoxyacetate 
• 1213265-26-9 (S)-benzyl 2-((2S,4R,6R)-tetrahydro-6-((2S,3S,4R)-2,4-bishydroxy-3-methyl-5-(6-methyl-2-methyloxycarbonyl-3,5-bistriisopropylsilyloxyphenyl)-pentyl)-5,5-dimethyl-4-tert-butyldimethylsilyloxy-2H-pyran-2-yl)-2-methoxyacetate 
• 1213264-84-6 (S)-benzyl 2-((2S,4R,6R)-tetrahydro-6-((2S,3S)-3-((3R)-6,8-bistriisopropylsilyloxy-5-methyl-3,4-dihydroisocoumarinyl)-3-methyl-2-tert-butyldimethylsilyloxypropyl)-5,5-dimethyl-4-tert-butyldimethylsilyloxy-2H-pyran-2-yl)-2-methoxyacetate 

Relevant academic research and scientific papers

Total Synthesis and Biological Evaluation of Irciniastatin A (a.k.a. Psymberin) and Irciniastatin B

Irciniastatin A (a.k.a. psymberin) and irciniastatin B are members of the pederin natural product family, which have potent antitumor activity and structural complexity. Herein, we describe a full account of our total synthesis of (+)-irciniastatin A and (-)-irciniastatin B. Our synthesis features the highly regioselective Eu(OTf)3-catalyzed, DTBMP-assisted epoxide ring opening reaction with MeOH, which enabled a concise synthesis of the C1-C6 fragment, extensive use of AZADO (2-azaadamantane N-oxyl) and its related nitroxyl radical/oxoammonium salt-catalyzed alcohol oxidation throughout the synthesis, and a late-stage assembly of C1-C6, C8-C16, and C17-C25 fragments. In addition, for the synthesis of (-)-irciniastatin B, we achieved the C11-selective control of the oxidation stage via regioselective deprotection and AZADO-catalyzed alcohol oxidation. The synthetic irciniastatins showed high levels of cytotoxic activity against mammalian cells. Furthermore, chemical footprinting experiments using synthetic compounds revealed that the binding site of irciniastatins is the E-site of the ribosome.

Syntheses and biological evaluation of irciniastatin A and the C1-C2 alkyne analogue

Chemical equation presented Syntheses of both natural (+)- and unnatural (-)-irciniastatin A (aka psymberin) as well as a C1-C2 alkyne analogue of (+)-irciniastatin A have been achieved. The key features of the syntheses include a highly regioselective epoxide-opening reaction and a late-stage assembly of C1-C6, C8-C16, and C17-C25 fragments. (+)-Alkymberin retained a high level of cytotoxicity, whereas (-)-irciniastatin A showed almost no activity. These results suggest that (+)-alkymberin could be a useful enantio-differential probe for mode-of-action study.