618096-58-5

Upstream product

• 78878-05-4 1-iodo-3-(tert-butyldimethylsilyloxy)propane 
• 192060-67-6 (1R,2R)-(-)-pseudoephedrinepropionamide 

Downstream Products

• 529494-90-4 (2R,4R,5S)-8-(tert-Butyl-dimethyl-silanyloxy)-1-{(2R,4R,6S)-6-[2-(4-methoxy-benzyloxy)-ethyl]-4-triisopropylsilanyloxy-tetrahydro-pyran-2-yl}-5-methyl-octane-2,4-diol 
• 618096-72-3 (2R,4R,5S)-8-(tert-Butyl-dimethyl-silanyloxy)-1-{(2R,4S,6S)-6-[2-(4-methoxy-benzyloxy)-ethyl]-4-triisopropylsilanyloxy-tetrahydro-pyran-2-yl}-5-methyl-octane-2,4-diol 
• 1612233-48-3 (S)-5-(7-((tert-butyldimethylsilyl)oxy)-4-methylhepta-1,2-dien-3-yl)-2-(phenylthio)oxazole 
• 1612233-49-4 (S)-4-bromo-5-(7-((tert-butyldimethylsilyl)oxy)-4-methylhepta-1,2-dien-3-yl)-2-(phenylthio)oxazole 
• 1612233-50-7 (S)-4-methyl-5-(2-(phenylthio)oxazol-5-yl)hepta-5,6-dien-1-ol 
• 1612233-52-9 (S)-4-methyl-5-(2-(phenylthio)oxazol-5-yl)hepta-5,6-dienal 
• 1612233-54-1 (S)-5-(4-methylocta-1,2-dien-7-yn-3-yl)-2-(phenylthio)oxazole 
• 1612233-51-8 (S)-5-(4-bromo-2-(phenylthio)oxazol-5-yl)-4-methylhepta-5,6-dien-1-ol 
• 1612233-53-0 (S)-5-(4-bromo-2-(phenylthio)oxazol-5-yl)-4-methylhepta-5,6-dienal 
• 1612233-55-2 (S)-4-bromo-5-(4-methylocta-1,2-dien-7-yn-3-yl)-2-(phenylthio)oxazole 
• 1612233-56-3 (S)-6-methyl-7-(2-(phenylthio)oxazol-5-yl)-5,6-dihydro-1H-inden-2(4H)-one 
• 1612233-57-4 (S)-7-(4-bromo-2-(phenylthio)oxazol-5-yl)-6-methyl-5,6-dihydro-1H-inden-2(4H)-one 
• 1612233-59-6 (S)-6-methyl-1-methylene-7-(2-(phenylthio)oxazol-5-yl)-5,6-dihydro-1H-inden-2(4H)-one 
• 1612233-60-9 (S)-7-(4-bromo-2-(phenylthio)oxazol-5-yl)-6-methyl-1-methylene-5,6-dihydro-1H-inden-2(4H)-one 

Relevant academic research and scientific papers

Total synthesis of (+)-ileabethoxazole via an iron-mediated pauson-khand [2 + 2 + 1] carbocyclization

Studies describe the total synthesis of (+)-ileabethoxazole (1) using a Stille cross-coupling reaction of propargylic stannanes with 5-iodo-1,3-oxazoles to produce 1,1-disubstituted allenes (11). An iron-mediated [2 + 2 + 1] carbocyclization yields a novel cyclopentenone for elaboration to 1. Site-selective palladium insertion reactions allow for regiocontrolled substitutions of the heterocycle. Asymmetric copper hydride reductions are examined, and strategies for the formation of the central aromatic ring are discussed.

A fully stereocontrolled total synthesis of (+)-leucascandrolide A

A highly stereocontrolled total synthesis of leucascandrolide A, a cytotoxic 18-membered macrolide from the calcareous sponge Leucascandra caveolata, starts out with a Jacobsen asymmetric hetero Diels-Alder reaction to configure the 2,6-cis-tetrahydropyran ring. All the remaining oxygenated stereocentres are introduced with high selectivity by relying on substrate-based control. An efficient endgame depends on two Mitsunobu reactions, the first to close the macrolactone with inversion at C17 and the second to attach the oxazole-containing side chain at C5, followed by Lindlar hydrogenation of the two alkynes to provide (+)-leucascandrolide A.