309241-36-9

Upstream product

• 207789-80-8 (E)-(R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-iodo-3,4-dimethyl-pent-4-enal 
• 207789-85-3 (3R,4S,5R,7S)-3,4-bis(tert-butyldimethylsilyloxy)-7-(4-methoxybenzyloxy)-5-methyloctan-2-one 
• 6153-06-6 (E)-3-methylpent-2-en-4-yn-1-ol 
• 72345-23-4 (2S,4S)-pentane-2,4-diol 
• 824-94-2 p-methoxybenzyl chloride 
• 207789-81-9 Toluene-4-sulfonic acid (1S,3S)-3-(4-methoxy-benzyloxy)-1-methyl-butyl ester 
• 118759-62-9 ((2S,3S)-3-Ethynyl-3-methyl-oxiranyl)-methanol 
• 207789-84-2 (3R,4S,5R,7S)-3,4-Dihydroxy-7-(4-methoxy-benzyloxy)-5-methyl-octan-2-one 
• 207789-78-4 (E)-(R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2,3-dimethyl-1-trimethylsilanyl-pent-1-ene 
• 207789-83-1 (E)-(5R,7S)-7-(4-Methoxy-benzyloxy)-5-methyl-oct-3-en-2-one 
• 207789-79-5 (E)-(R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-1-iodo-2,3-dimethyl-pent-1-ene 
• 207789-82-0 (2R,4S)-4-(4-Methoxy-benzyloxy)-2-methyl-pentanenitrile 
• 274693-86-6 (2R,4S)-4-(4-Methoxy-benzyloxy)-2-methyl-pentanal 
• 207789-88-6 (E)-(R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-iodo-3,4-dimethyl-pent-4-en-1-ol 

Downstream Products

• 309241-55-2 (E)-(3R,5S,8R,9S,10R,12S)-3,8,9-Tris-(tert-butyl-dimethyl-silanyloxy)-1-iodo-12-(4-methoxy-benzyloxy)-2,3,10-trimethyl-5-triethylsilanyloxy-tridec-1-en-7-one 

Relevant academic research and scientific papers

Towards the synthesis of amphidinolide B. An intramolecular stille coupling approach

A synthetic approach towards the cytotoxic polyene polyol macrolide amphidinolide B (1), based on elaboration of the C1-C13 carboxylic acid 4. and the C14-C25 alcohol 3 units, their esterification to the iodostannyl ester 2, and an intramolecular Stille sp2-sp2 coupling reaction, is described. In spite of adequate precedent and model experiments, circumstances conspired and the aforementioned coupling reaction was not realised in this case. (C) 2000 Elsevier Science Ltd.

Studies Towards a Total Synthesis of Amphidinolide B. Stereocontrolled Synthesis of the C14-C26 Polyol Fragment

A practical synthesis of the C14-C26 polyol unit 2 in amphidinolides B1 and B2, 1, is described which involves elaboration of the chiral unsaturated aldehyde 4 and the chiral ketone 5, followed by crossed-aldolisation of 4 and 5 in the presence of LiHMDS at -78 deg C, as key steps.