91920-88-6

Usage

InChI:InChI=1/C33H60O7/c1-10-13-19(2)18-22(5)29(35)20(3)14-11-12-15-27(34)23(6)30(36)25(8)31(37)26(9)32-21(4)16-17-28(40-32)24(7)33(38)39/h11,14,18-21,23-32,34-37H,10,12-13,15-17H2,1-9H3,(H,38,39)/b14-11+,22-18+

Upstream product

• 781652-01-5 (S)-(4,4-dibromo-2-methylbut-3-enyloxy)triisopropylsilane 
• 781652-03-7 (3Z,5E)-(S)-2,4-Dimethyl-nona-3,5-dien-1-ol 
• 1026286-03-2 (2R,4R)-4-{(2S,5S,6S)-6-[(S)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-5-methyl-tetrahydro-pyran-2-yl}-pentane-2,3-diol 
• 628293-10-7 methyl (2S)-2-((2S,5S,6S)-6-{(1R,2R,3R,5S,6R,9E,11R,12R,13E,15R)-2,12-bis[(tert-butyldimethylsilyl)oxy]-6-hydroxy-1,3,5,11,13,15-hexamethyl-4-oxooctadi-9,13-enyl}-5-methyltetrahydro-2H-pyran-2-yl)propanoate 
• 1026334-87-1 Methanesulfonic acid (E)-(3R,6R,7R)-12-benzyloxy-6-methoxymethoxy-1,3,5,7-tetramethyl-dodec-4-en-8-ynyl ester 
• 1026590-46-4 [(E)-(1R,4R)-1-((E)-(R)-6-Benzyloxy-1-methyl-hex-2-enyl)-2,4-dimethyl-hept-2-enyloxy]-tert-butyl-dimethyl-silane 
• 628292-97-7 methyl (2S)-2-((2S,5S,6S)-6-{[(1R,2R,3R)-2-(tert-butyldimethylsilyl)oxy]-1,3-dimethyl-4-oxohexyl}-5-methyltetrahydro-2H-pyran-2-yl)propanoate 
• 628293-01-6 methyl (2S)-2-((2S,5S,6S)-6-{(1S,2S,3S)-2-[(tert-butyldimethylsilyl)oxy]-1,3-dimethylpent-4-enyl}-5-methyltetrahydro-2H-pyran-2-yl)propanoate 
• 628293-06-1 (E)-(4R,7R,8R)-13-benzyloxy-7-methoxymethoxy-4,6,8-trimethyltridec-5-en-9-yn-2-one 
• 725724-80-1 (2RS,4R,5E,7R,8R)-13-benzyloxy-7-methoxymethoxy-4,6,8-trimethyltridec-5-en-9-yn-2-ol 
• 628293-07-2 (6R,7R,8E,10R)-1-benzyloxy-7-methoxymethoxy-6,8,10-trimethyltridec-8-en-4-yne 
• 725724-81-2 (4E,6R,7R,8E,10R)-7-[(tert-butyldimethylsilyl)oxy]-6,8,10-trimethyltrideca-4,8-dien-1-ol 
• 628293-09-4 (4E,6R,7R,8E,10R)-1-benzyloxy-6,8,10-trimethyltrideca-4,8-dien-7-ol 
• 628293-08-3 (6R,7R,8E,10R)-1-benzyloxy-6,8,10-trimethyltridec-8-en-4-yn-7-ol 

Relevant academic research and scientific papers

Stereoselective total synthesis of the ionophore antibiotic zincophorin

Acyclic stereocontrol is the basis of an original strategy adopted for the first, highly stereoselective total synthesis of the free acid zincophorin (1), a unique ionophore antibiotic. The stereoselective synthesis of the trisubstituted tetrahydropyran moiety and the construction of the eight contiguous stereogenic centers were key challenges in the synthesis.

Total synthesis of zincophorin and its methyl ester

A total synthesis of the naturally occurring ionophore zincophorin has been realized. The route features an intramolecular oxymercuration of a cyclopropanemethanol and a Carroll-Claisen rearrangement for the respective elaboration of the C1-C12 and C13-C25 subunits, which have been assembled by using a highly diastereoselective titanium-mediated aldol condensation.

Total synthesis of zincophorin

The total synthesis of the title compound, which is a zinc-binding antibiotic, is described. The synthesis starts with aldehyde 4 and Grignard reagent 6. The key steps are (i) the cyclocondensation of aldehyde 10 with diene 11 under the influence of magnesium bromide, (ii) the cyclocondensation of aldehyde 24 with diene 33 under the influence of BF3·OEt2, (iii) the carbon Ferrier reaction of glycal acetate 37 with (E)-crotyltrimethylsilane, and (iv) the reductive merger of aldehyde 2a with sulfone 3.