247200-11-9

Upstream product

• 247200-09-5 Toluene-4-sulfonic acid (E)-(1S,4R,5R,8S,9R)-14-benzyloxy-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-8-hydroxy-9-methoxymethoxy-1-((R)-1-methoxymethoxy-undecyl)-tetradec-10-enyl ester 
• 247200-05-1 Toluene-4-sulfonic acid (E)-(1S,2R)-1-[(3R,4R)-7-benzyloxy-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-heptyl]-2-methoxymethoxy-dodec-3-enyl ester 
• 247200-06-2 Toluene-4-sulfonic acid (1S,2R)-1-[(3R,4R)-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-7-hydroxy-heptyl]-2-methoxymethoxy-dodecyl ester 
• 247200-07-3 Toluene-4-sulfonic acid (1S,2R)-1-[(3R,4R)-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-7-oxo-heptyl]-2-methoxymethoxy-dodecyl ester 
• 247200-04-0 (E)-(4R,5R,8S,9R)-1-Benzyloxy-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-9-methoxymethoxy-nonadec-10-en-8-ol 
• 204572-66-7 (4R,5R)-8-Benzyloxy-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-octanal 
• 247200-10-8 C₆₂H₁₀₄O₁₃S₂Si₂ 

Downstream Products

• 156162-01-5 asimin 

Relevant academic research and scientific papers

Total synthesis of the cytotoxic threo, trans, threo, trans, threo annonaceous acetogenin asimin and its C-10 epimer: Unambiguous confirmation of absolute stereochemistry

A convergent synthesis of asimin (1) and its C-10 epimer 33 is reported. The essential features of this synthesis include (a) the addition of an enantioenriched γ-OMOM allylic indium reagent to a core C-23 aldehyde precursor to install the C-24-C-34 segment with concomitant introduction of the C-24 and C-23 stereocenters; (b) the addition of an enantioenriched γ- OMOM allylic indium reagent to a core C-16 aldehyde to install the C-10-C-15 segment with formation of the C-15 and C-16 stereocenters, (c) the addition of a dialkyl zinc reagent, catalyzed by a Chiral triflamide-Ti(O-i-Pr)4 complex, to introduce the C-1-C-9 segment with creation of either the 10(R) or 10(S) stereocenters; and (d) aldol condensation of the foregoing C-1-C-34 segment with OTBS-protected lactic aldehyde to incorporate the C-35-C-37 butenolide segment. Removal of the three MOM protecting groups was achieved with aqueous HCl in THF. The 10(R) diastereomer was found to correspond to natural asimin.