934497-74-2

Upstream product

• 1399680-07-9 (2S,6S,7S,E)-2,6-dimethyl-7-((triethylsilyl)oxy)non-4-en-1-yl methanesulfonate 
• 1399680-36-4 C₁₂H₂₄O₄S 
• 95273-27-1 (3S,4S)-4-hydroxy-3-methyl-1-hexene 
• 1399679-64-1 (S)-2-methylpent-4-en-1-yl methanesulfonate 

Downstream Products

• 934497-75-3 (2R,3S)-2-((2R,3R)-3-{(2S)-2-methyl-3-[(1-phenyl-1H-tetrazol-5-yl)sulfonyl]propyl}oxiran-2-yl)pentan-3-ol 
• 1399679-51-6 5-(((S)-2-methyl-3-((2R,3R)-3-((2S,3S)-3-((triethylsilyl)oxy)pentan-2-yl)oxiran-2-yl)propyl)sulfonyl)-1-phenyl-1H-tetrazole 
• 445493-23-2 (2S,3S,6S,7R,10R,E)-7,10-dihydroxy-2-{(S,2E,4E)-7-[(2R,3R)-3-{(2R,3S)-3-hydroxypentan-2-yl}oxiran-2-yl]-6-methylhepta-2,4-dien-2-yl}-3,7-dimethyl-12-oxooxacyclododec-4-en-6-yl acetate 
• 934497-76-4 C₁₈H₂₄N₄O₄S 

Relevant academic research and scientific papers

Enantioselective total synthesis of pladienolide B: A potent spliceosome inhibitor

An enantioselective and convergent total synthesis of pladienolide B (1) is described. Pladienolide B binds to the SF3b complex of a spliceosome and inhibits mRNA splicing activity. The synthesis features an epoxide opening reaction, an asymmetric reduction of a β-keto ester, and a cross metathesis strategy for the side chain synthesis.

Process for total synthesis of pladienolide B and pladienolide D

[Problems to be Solved] To provide an effective process for total synthesis of pladienolide B and pladienolide D having excellent anti-tumor activity and to provide useful intermediates in the above-described process. [Measure for Solving the Problem] A process for producing a compound represented by Formula (11): wherein P1, P7, P8, P9 and R1 are the same as defined below, characterized by including reacting a compound represented by Formula (12): wherein P7 means a hydrogen atom or a protecting group for hydroxy group; R1 means a hydrogen atom or a hydroxy group, with a compound represented by Formula (13): wherein P1 means a hydrogen atom or a protecting group for hydroxy group; P8 means a hydrogen atom, an acetyl group or a protecting group for hydroxy group; P9 means a hydrogen atom or a protecting group for hydroxy group; or P8 and P9 may form together a group represented by a formula: wherein R5 means a phenyl group which may have a substituent, in the presence of a catalyst.

Total synthesis of the potent antitumor macrolides pladienolide B and D

Getting cross: The total syntheses of two pladienolides (see picture), which have prominent antitumor activity based on a unique mechanism of action, have been accomplished, and their absolute configurations were verified. The 12-membered aliphatic macrolide structure was formed by ring-closing metathesis, and the side-chain moiety was coupled to the macrolide by Julia-Kocienski olefination or cross-metathesis. (Chemical Equation Presented).