134699-11-9

Upstream product

• 61550-02-5 (furan-2-yloxy)-trimethylsilane 
• 10486-19-8 tridecanal 
• 6064-48-8 1-hydroxy-2(E)-pentadecene 
• 2907-52-0 2-pentadecen-1-ol 

Downstream Products

• 676441-72-8 (S)-3-((E)-(13R,14R,17S,18S)-13-Hydroxy-14,17,18-tris-methoxymethoxy-triacont-8-en-10-ynyl)-5-methyl-3-phenylsulfanyl-dihydro-furan-2-one 
• 676441-73-9 (S)-3-((13R,14R,17S,18S)-13-Hydroxy-14,17,18-tris-methoxymethoxy-triacontyl)-5-methyl-3-phenylsulfanyl-dihydro-furan-2-one 

Relevant academic research and scientific papers

Synthesis of (+)-(4S,5S)-muricatacin via Pd-catalyzed stereospecific hydroxy substitution reaction of γ,δ-epoxy α,β- unsaturated ester with B(OH)3

The stereoselective synthesis of (+)-(4S,5S)-muricatacin has been achieved involving the palladium-catalyzed stereospecific hydroxy substitution reaction of γ,δ-epoxy α,β-unsaturated ester with B(OH) 3.

De novo asymmetric syntheses of muricatacin and its analogues via dihydroxylation of dienoates

A short and highly efficient route to both enantiomers of muricatacin as well as the C-5-epimer has been developed. The key to the overall transformation is the highly regio- and enantioselective Sharpless asymmetric dihydroxylation of an (E,Z)-dienoate. The highly efficient stereoselective synthesis prepares (-)-muricatacin in seven steps and 66% overall yield.

Highly Enantioselective 1,2-Addition of 2-[(Trimethylsilyl)oxy]furan to Aldehydes: Application to Muricatacin Synthesis

TMSOF 2-[(trimethylsilyl)oxy]furan has been used in an enantioselective aldol reaction for the first time. Indeed, addition of TMSOF to achiral aldehydes, in the presence (R)-1,1-bi-2-naphthol (Binol), gave the corresponding butenolides with moderate diastereomeric ratios (dr = 60%) and ee's between 60 and 90%. Application of this reaction to the total synthesis of annonaceous muricatacin in only two steps (in regards to the numerous multistep syntheses published so far) illustrated the efficiency of this strategy.