1186291-38-2

Upstream product

• 1186291-52-0 C₃₀H₅₄O₆Si₂ 

Downstream Products

• 1186291-39-3 C₄₂H₆₇NO₆S₂Si₂ 
• 1213265-24-7 (R)-benzyl 2-((2R,4S,6S)-tetrahydro-5,5-dimethyl-6-((3R,4S)-4-hydroxy-3-methyl-5-(6-methyl-2-methyloxycarbonyl-3,5-bistriisopropylsilyloxyphenyl)-2-oxopentyl)-4-tert-butyldimethylsilyloxy-2H-pyran-2-yl)-2-methoxyacetate 
• 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 

Relevant academic research and scientific papers

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.

Total synthesis of irciniastatin A (psymberin)

The total synthesis of (+)-iriciniastatin A (psymberin) is reported in 19 steps and 6% overall yield. Key reactions include a highly convergent enolsilane-oxocarbenium ion union to generate the C8-C25 fragment and a late-stage coupling of a hemiaminal and