866148-39-2

Upstream product

• 79271-56-0 triethylsilyl trifluoromethyl sulfonate 
• 4392-24-9 3-bromo-1-phenyl-1-propenyl bromide 
• 4392-24-9 Cinnamyl bromide 
• 866148-31-4 (E)-(4R,9R)-4,5,9-Trimethyl-7-methylene-1-phenyl-4-triethylsilanyloxy-10-triisopropylsilanyloxy-dec-1-en-5-ol 
• 866148-27-8 (2S,5R)-2-tert-Butyl-5-methyl-5-((E)-3-phenyl-allyl)-[1,3]dioxolan-4-one 
• 866148-45-0 (E)-(R)-3-Hydroxy-3-methyl-6-phenyl-hex-5-en-2-one 
• 866148-44-9 (R)-2-Methyl-4-trimethylsilanylmethyl-pent-4-en-1-ol 
• 866148-38-1 (E)-(3R,8R)-3,8-Dimethyl-5,7-dimethylene-11-phenyl-8-triethylsilanyloxy-undec-10-enenitrile 
• 866148-30-3 (R)-4-Methyl-5-triisopropylsilanyloxy-2-trimethylsilanylmethyl-pent-1-ene 
• 866148-28-9 (E)-(R)-3-Methyl-6-phenyl-3-triethylsilanyloxy-hex-5-en-2-one 
• 866148-29-0 (S)-4-Benzyl-3-((R)-2-methyl-4-trimethylsilanylmethyl-pent-4-enoyl)-oxazolidin-2-one 
• 866148-49-4 (E)-(3R,8R)-8-Hydroxy-3,8-dimethyl-5,7-dimethylene-11-phenyl-undec-10-enenitrile 
• 866148-35-8 (E)-(2R,7R)-2,7-Dimethyl-4,6-dimethylene-10-phenyl-dec-9-ene-1,7-diol 

Relevant academic research and scientific papers

Amphidinolide B: Total synthesis, structural investigation, and biological evaluation

The total syntheses of amphidinolide B1 and the proposed structure of amphidinolide B2 have been accomplished. Key aspects of this work include the development of a practical, non-transition-metal-mediated method for the construction of the C13-C15 diene, the identification of α-chelation and dipole minimization models for diastereoselective methyl ketone aldol reactions, the discovery of a spontaneous Horner-Wadsworth-Emmons macrocyclization strategy, and the development of a novel late stage method for construction of an allylic epoxide moiety. The originally proposed structure for amphidinolide B2 and diastereomers thereof display potent antitumor activities with IC50 values ranging from 3.3 to 94.5 nM against human solid and blood tumor cells. Of the different stereoisomers, the proposed structure of amphidinolide B2 is over 12-fold more potent than the C8,9-epimer and C18-epimer in human DU145 prostate cancer cells. These data suggest that the epoxide stereochemistry is a significant factor for anticancer activity.

Synthetic studies toward amphidinolide B1: Synthesis of the C9-C26 fragment

(Chemical Equation Presented) The synthesis of the C9-C 26 portion of amphidinolide B1 is described. A Fleming allylation followed by elimination was employed for the construction of the C13-C15 diene portion. Sharpless asymmetric dihydroxylation was utilized for regioselective functionalization of a styrene-derived alkene, in the presence of the C13-C15 diene functionality. A highly diastereoselective aldol reaction was developed to establish the C18 stereochemistry.