250355-86-3

Upstream product

• 288092-41-1 2-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2,3-dihydro-pyran-4-one 
• 799852-47-4 (2S,6S)-2-Allyl-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-tetrahydro-pyran-4-one 
• 250355-82-9 (-)-(2S)-2-[2-(tert-butyldiphenylsiloxy)ethyl]-2H-pyran-4(3H)-one 
• 112897-03-7 3-(tert-butyldiphenylsilyloxy)-1-propanal 
• 867033-51-0 {6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-4-oxo-tetrahydro-pyran-2-yl}-thioacetic acid S-ethyl ester 
• 867033-52-1 {6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-4-methylene-tetrahydro-pyran-2-yl}-thioacetic acid S-ethyl ester 

Downstream Products

• 799852-52-1 {2-[(2R,6R)-6-(3-Bromo-prop-2-ynyl)-4-methylene-tetrahydro-pyran-2-yl]-ethoxy}-tert-butyl-diphenyl-silane 
• 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 
• 250355-97-6 4-((2R,4R,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-6-{(2R,6R)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-4-methylene-tetrahydro-pyran-2-ylmethyl}-tetrahydro-pyran-2-yl)-2-(4-methoxy-benzyloxymethyl)-oxazole 
• 250355-94-3 (2R,6R)-2-{(2R,6R)-6-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-4-methylene-tetrahydro-pyran-2-ylmethyl}-6-[2-(4-methoxy-benzyloxymethyl)-oxazol-4-yl]-tetrahydro-pyran-4-one 
• 250355-98-7 [4-((2R,4R,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-6-{(2R,6R)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-4-methylene-tetrahydro-pyran-2-ylmethyl}-tetrahydro-pyran-2-yl)-oxazol-2-yl]-methanol 
• 867033-56-5 C₆₁H₈₆INO₉Si₂ 
• 867033-66-7 2-{6-[4-(tert-butyl-dimethyl-silanyloxy)-6-(2-{3-[4-(3,4-dimethoxy-benzyloxy)-6-(2-iodo-1-methyl-vinyl)-3,5-dimethyl-tetrahydro-pyran-2-yl]-propenyl}-oxazol-4-yl)-tetrahydro-pyran-2-ylmethyl]-4-methylene-tetrahydro-pyran-2-yl}-ethanol 
• 867033-68-9 {6-[4-(tert-butyl-dimethyl-silanyloxy)-6-(2-{3-[4-(3,4-dimethoxy-benzyloxy)-6-(2-iodo-1-methyl-vinyl)-3,5-dimethyl-tetrahydro-pyran-2-yl]-propenyl}-oxazol-4-yl)-tetrahydro-pyran-2-ylmethyl]-4-methylene-tetrahydro-pyran-2-yl}-acetaldehyde 
• 867033-50-9 Methanesulfonic acid 4-((2R,4R,6R)-4-(tert-butyl-dimethyl-silanyloxy)-6-{(2R,6R)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-4-methylene-tetrahydro-pyran-2-ylmethyl}-tetrahydro-pyran-2-yl)-oxazol-2-ylmethyl ester 

Relevant academic research and scientific papers

(+)-Phorboxazole a synthetic studies. A highly convergent, second generation total synthesis of (+)-phorboxazole A

(Chemical Equation Presented) A second generation total synthesis of the potent antitumor agent (+)-phorboxazole A (1) has been achieved. The cornerstone of this approach comprises a more convergent strategy, involving late-stage Stille union of a fully e

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.

Total synthesis of (+)-phorboxazole A exploiting the Petasis-Ferrier rearrangement

A highly convergent, stereocontrolled total synthesis of the potent antiproliferative agent (+)-phorboxazole A (1) has been achieved. Highlights of the synthesis include: modified Petasis-Ferrier rearrangements for assembly of both the C(11 - 15) and C(22-26) cis-tetrahydropyran rings; extension of the Julia olefination to the synthesis of enol ethers; the design, synthesis, and application of a novel bifunctional oxazole linchpin; and Stille coupling of a C(28) trimethyl stannane with a C(29) oxazole triflate. The longest linear sequence leading to (+)-phorboxazole A (1) was 27 steps, with an overall yield of 3%.