197227-76-2

Upstream product

• 197228-05-0 2,2-Dimethyl-propionic acid (E)-(3S,4R,5R)-3-(tert-butyl-dimethyl-silanyloxy)-5-methoxy-8-(4-methoxy-benzyloxy)-4,6-dimethyl-oct-6-enyl ester 
• 197228-04-9 2,2-Dimethyl-propionic acid (E)-(3S,4S,5R)-3-hydroxy-5-methoxy-8-(4-methoxy-benzyloxy)-4,6-dimethyl-oct-6-enyl ester 
• 197228-01-6 (2E,6E)-(4S,5R)-5-Methoxy-8-(4-methoxy-benzyloxy)-4,6-dimethyl-octa-2,6-dienoic acid methyl ester 
• 197227-70-6 (2E)-4-[(4-methoxybenzyl)oxy]-2-methylbut-2-enal 
• 147438-60-6 (E)-(2R,3R)-3-Methoxy-6-(4-methoxy-benzyloxy)-2,4-dimethyl-hex-4-enal 
• 197227-72-8 (E)-(2S,3R)-3-Methoxy-6-(4-methoxy-benzyloxy)-2,4-dimethyl-hex-4-en-1-ol 
• 197227-96-6 (E)-(2S,3R)-6-(4-Methoxy-benzyloxy)-2,4-dimethyl-hex-4-ene-1,3-diol 
• 219606-81-2 (3R,4S)-4,6-bis(tert-butyldimethylsilyloxy)-3-methylhex-1-ene 
• 188926-25-2 (2S,3S)-3,5-bis{[tert-butyl(dimethyl)silyl]oxy}-2-methylpentanal 
• 168777-81-9 (3S,4R)-1-[(tert-butyldimethylsilyl)oxy]-4-methylhex-5-en-3-ol 
• 850697-71-1 1-[(E)-(4R,5R,6S)-6,8-Bis-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-3,5-dimethyl-oct-2-enyloxymethyl]-4-methoxy-benzene 
• 850697-65-3 (E)-(4R,5R,6S)-6,8-Bis-(tert-butyl-dimethyl-silanyloxy)-1-(4-methoxy-benzyloxy)-3,5-dimethyl-oct-2-en-4-ol 
• 850697-63-1 1-((E)-3-Iodo-but-2-enyloxymethyl)-4-methoxy-benzene 
• 197228-06-1 (E)-(3S,4R,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-methoxy-8-(4-methoxy-benzyloxy)-4,6-dimethyl-oct-6-en-1-ol 

Downstream Products

• 691869-42-8 (Diethoxy-phosphoryl)-acetic acid (4E,6E)-(1S,3S,8R)-1-[(E)-(1S,2R)-2-methoxy-5-(4-methoxy-benzyloxy)-1,3-dimethyl-pent-3-enyl]-4-methyl-8-[(2R,4S)-6-oxo-4-(2-oxo-ethyl)-tetrahydro-pyran-2-yl]-3-triisopropylsilanyloxy-nona-4,6-dienyl ester 
• 691869-54-2 (3E,10E,12E)-(1R,7S,9S,14R,15R)-7-[(E)-(1S,2R)-2-Methoxy-5-(4-methoxy-benzyloxy)-1,3-dimethyl-pent-3-enyl]-10,14-dimethyl-9-triisopropylsilanyloxy-6,16-dioxa-bicyclo[13.3.1]nonadeca-3,10,12-triene-5,17-dione 
• 850697-82-4 (Diethoxy-phosphoryl)-acetic acid (4E,6E)-(1S,3S,8R)-8-[(2R,4R)-4-(2-hydroxy-ethyl)-6-oxo-tetrahydro-pyran-2-yl]-1-[(E)-(1S,2R)-2-methoxy-5-(4-methoxy-benzyloxy)-1,3-dimethyl-pent-3-enyl]-4-methyl-3-triisopropylsilanyloxy-nona-4,6-dienyl ester 
• 850697-74-4 (E)-(5S,6R,7R)-5-(tert-Butyl-dimethyl-silanyloxy)-7-methoxy-10-(4-methoxy-benzyloxy)-2,6,8-trimethyl-deca-1,8-dien-3-one 
• 850697-73-3 (E)-(5S,6R,7R)-5-(tert-Butyl-dimethyl-silanyloxy)-7-methoxy-10-(4-methoxy-benzyloxy)-2,6,8-trimethyl-deca-1,8-dien-3-ol 

Relevant academic research and scientific papers

Total synthesis of rhizoxin D

A total synthesis of rhizoxin D (1b), a 16-membered antitumoral macrolide, is reported. The strategy relies on the application of a Brown allylation reaction for the C15 and C16 asymmetric centres control. Installation of the C17 hydroxyl function with concomitant building of the (E)-C18-C19 double bond was effected by a diastereoselective addition of vinyllithium derivative 15 to aldehyde 10. The terminal enone group was then introduced to achieve the preparation of C11-C20 segment 23. A Heck coupling reaction between C11-C20 fragment 23 and C3-C10 segment 24 (previously prepared in our laboratory) was performed with success to deliver the C3-C20 fragment 25. The total synthesis of rhizoxin D (1b) was achieved after transformation of 25 into the macrolactone 28, and coupling the C21-C28 side chain using a Wittig-Wadsworth-Emmons reaction. Georg Thieme Verlag Stuttgart.

Total synthesis of rhizoxin D

The convergent, enantiocontrolled synthesis of a significant antimitotic agent for cancer chemotherapy is presented with completion of rhizoxin diene 2.