799852-47-4

Upstream product

• 24850-33-7 allyltributylstanane 
• 288092-41-1 2-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2,3-dihydro-pyran-4-one 

Downstream Products

• 799852-54-3 4-{(2R,6R)-6-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-4-methylene-tetrahydro-pyran-2-yl}-but-2-ynoic acid methyl ester 
• 799852-50-9 tert-Butyl-{2-[(2R,6S)-6-(3,3-dibromo-allyl)-4-methylene-tetrahydro-pyran-2-yl]-ethoxy}-diphenyl-silane 
• 799852-52-1 {2-[(2R,6R)-6-(3-Bromo-prop-2-ynyl)-4-methylene-tetrahydro-pyran-2-yl]-ethoxy}-tert-butyl-diphenyl-silane 
• 250355-86-3 {(2R,6R)-6-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-4-methylene-tetrahydro-pyran-2-yl}-acetaldehyde 

Relevant academic research and scientific papers

Phorboxazole B synthetic studies: Construction of C(1-32) and C(33-46) subtargets

The convergent syntheses of the C(1-32) and C(33-46) domains of phorboxazole B are described. An iterative cyclocondensation strategy exploited the Jacobsen hetero-Diels-Alder (HDA) reaction as a platform for the synthesis of both the C(5-9) and C(11-15) tetrahydropyran rings. The use of 2-silyloxydiene coupling partners bearing an increasing resemblance to the phorboxazole skeleton was found to lead to a reduction in diastereoselectivity, however, in the case of the C(11-15) ring. The coupling of aldehyde 21 and 2-silyloxydiene 20 by this route provided a C(1-32) fragment which was elaborated to the macrolide core of phorboxazole B. The synthesis of the C(33-46) domain involved a Nozaki-Kishi coupling of aldehyde 31 and vinyl iodide 39. The syntheses of 31 and 39 were highly diastereoselective: an Evans [Cu(Ph-pybox)](SbF6)2-catalysed Mukaiyama aldol reaction formed the cornerstone of the synthesis of 31 whilst a Nagao-Fujita acetate aldol reaction provided a convenient means of installing the sole stereogenic centre of 39.