145285-58-1

Upstream product

• 122-78-1 phenylacetaldehyde 
• 2243-53-0 trans-styrylacetic acid 
• 91083-82-8 (E)-methyl 4-phenylbut-3-enoate 

Downstream Products

• 932739-30-5 (3R,4R,5R)-4-hydroxy-3-methyl-5-phenyl-tetrahydrofuran-2-one 
• 352214-90-5 ((4R,5R)-2,2-Dimethyl-5-phenyl-[1,3]dioxolan-4-yl)-acetic acid methyl ester 

Relevant academic research and scientific papers

Sharpless Asymmetric Dihydroxylation on α,β-Unsaturated Diazoketones: A New Entry for the Synthesis of Disubstituted Furanones

The synthesis of enantiomerically pure 4,5-disubstituted 2-furanones is accomplished in three steps from aldehydes. The steps involve a highly enantioselective Sharpless asymmetric dihydroxylation of α,β-unsaturated diazoketones, followed by a photochemical Wolff rearrangement.

Efficient synthesis of cryptophycin-52 and novel para- Alkoxymethyl unit A analogues

Cryptophycins are a family of highly cytotoxic, cyclic depsipeptides. They display antitumour activity that is largely maintained for multidrug-resistant tumour cells. Cryptophycins are composed of four building blocks (units A-D) that correspond to the respective amino and hydroxy acids. A new synthetic route to unit A allows the selective generation of all four stereogenic centres in a short, efficient and reliable synthesis and con-tributes to an easier and faster synthesis of cryptophycins. The first two stereogenic centres are introduced by a catalytic asymmetric dihydroxylation, whereas the remaining two stereogenic centres are introduced with substrate control of diastereoselectivity. The stereogenic diol function also serves as the epoxide precursor. The approach was used to synthesise the native unit A building block as well as three paraalkoxymethyl analogues from which cryptophycin-52 and three analogous cryptophycins were prepared. Macrocyclisation of the seco-depsipeptides was based on ring-closing metathesis.

Short and efficient synthesis of cryptophycin unit A

(Chemical Equation Presented) Two short synthetic approaches toward cryptophycin unit A comprise a catalytic asymmetric dihydroxylation as the sole source of chirality, while all further stereogenic centers are introduced under substrate control. The key

A four-step route from aldehydes to C2-elongated enantiomerically pure α,β-unsaturated γ-hydroxy esters

Asymmetric dihydroxylation of β,γ-unsaturated esters 4 provided β-hydroxy-γ-lactones 3 or ent-3. Methanolysis acetonide formation and LDA-mediated fragmentation of the resulting esters 5/ent-5 furnished the γ-chiral acrylates 6/ent-6 containing disubstitu

A general approach to γ-lactones via osmium-catalyzed asymmetric dihydroxylation. Synthesis of (-)- and (+)-muricatacin

Both enantiomers of hydroxy γ-lactones have been prepared highly enantioselectively (92-99% ee) using either AD-mix-β or AD-mix-α with both β,γ- and γ,δ-unsaturated esters. The method is exemplified by the three-step synthesis of (-) and (+)-muricatacin i