163564-92-9

Usage

Uses

Ratjadone A, Synthetic is a cell-permeable polyketide that inhibits cell proliferation.

InChI:InChI=1/C28H40O5/c1-6-9-26-22(5)25(30)18-27(33-26)24(29)12-7-10-19(2)16-21(4)17-20(3)14-15-23-11-8-13-28(31)32-23/h6-10,12-15,17,21-27,29-30H,11,16,18H2,1-5H3/b9-6+,12-7+,15-14+,19-10+,20-17-/t21-,22+,23-,24-,25-,26+,27+/m1/s1

Upstream product

• 321995-01-1 (2R,6R)-2-{(1E,3Z,7E,9E)-(5R,11R)-11-(tert-Butyl-dimethyl-silanyloxy)-11-[(2S,4R,5R,6S)-4-(tert-butyl-dimethyl-silanyloxy)-5-methyl-6-((E)-propenyl)-tetrahydro-pyran-2-yl]-3,5,7-trimethyl-undeca-1,3,7,9-tetraenyl}-6-isopropoxy-3,6-dihydro-2H-pyran 
• 321995-03-3 (2S,3R,4R,6S)-6-[(R)-1,2-Bis-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-(tert-butyl-dimethyl-silanyloxy)-3-methyl-2-((E)-propenyl)-tetrahydro-pyran 
• 321994-89-2 {(2R,3R)-3-[(E)-(2R,3S,4S)-2,4-Bis-(tert-butyl-dimethyl-silanyloxy)-3-methyl-hept-5-enyl]-oxiranyl}-methanol 
• 321995-04-4 (R)-2-(tert-Butyl-dimethyl-silanyloxy)-2-[(2S,4R,5R,6S)-4-(tert-butyl-dimethyl-silanyloxy)-5-methyl-6-((E)-propenyl)-tetrahydro-pyran-2-yl]-ethanol 
• 321995-06-6 (2S,3R,4R,6S)-4-(tert-Butyl-dimethyl-silanyloxy)-6-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-allyl]-3-methyl-2-((E)-propenyl)-tetrahydro-pyran 
• 321994-87-0 (2E,8E)-(5R,6S,7S)-5,7-Bis-(tert-butyl-dimethyl-silanyloxy)-6-methyl-deca-2,8-dien-1-ol 
• 321995-05-5 (S)-(tert-Butyl-dimethyl-silanyloxy)-[(2S,4R,5R,6S)-4-(tert-butyl-dimethyl-silanyloxy)-5-methyl-6-((E)-propenyl)-tetrahydro-pyran-2-yl]-acetaldehyde 
• 321995-00-0 (2R,6R)-2-((1E,3Z,7E)-(R)-8-Iodo-3,5,7-trimethyl-octa-1,3,7-trienyl)-6-isopropoxy-3,6-dihydro-2H-pyran 
• 331686-90-9 (E)-(2R,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-hex-4-enoic acid methoxy-methyl-amide 
• 321995-02-2 (E)-(2R,3S,4S)-1-((2R,3R)-3-Hydroxymethyl-oxiranyl)-3-methyl-hept-5-ene-2,4-diol 
• 321994-91-6 (R)-1-[(2S,4R,5S,6S)-4-Hydroxy-5-methyl-6-((E)-propenyl)-tetrahydro-pyran-2-yl]-ethane-1,2-diol 
• 321994-94-9 (2Z,6E)-(R)-7-Iodo-2,4,6-trimethyl-hepta-2,6-dienoic acid ethyl ester 
• 321995-08-8 (2Z,6E)-(R)-7-Iodo-2,4,6-trimethyl-hepta-2,6-dien-1-ol 
• 446859-99-0 (1E,5Z)-(R)-7-Bromo-1-iodo-2,4,6-trimethyl-hepta-1,5-diene 

Relevant academic research and scientific papers

The first total synthesis of (+)-ratjadone

The first total synthesis of ratjadone was achieved using a highly convergent approach joining three subunits together with a Wittig olefination and a selective Heck reaction as the pivotal steps. Besides establishing a robust and reliable route for the synthesis of this orphan ligand, the configuration of unknown stereocenters could also be determined. This synthesis not only provides an additional access to a biologically important compound but also enables the synthesis structural analogues for biological target identification.

Total synthesis of (-)-ratjadone.

[reaction in text] A convergent asymmetric synthesis of (-)-ratjadone (1) has been achieved, confirming the assignments of stereochemistry for the naturally occurring antifungal metabolite.

Total synthesis of (+)-ratjadone

The coupling of three fragmeats by a wittig olefination and a subsequent selective Heck reaction are the pivotal steps in the the first total synthesis of ratjadone (see picture), a cytotoxic as well as antibiotically effective polyketide. This synthesis enabled the elucidation of the absolute configuration of the natural product. In this way it should also be possible to synthesize structural analogues with which the various cellular processes mediated by ratjadone can be studied.