321868-49-9

Upstream product

• 4005-46-3 (1R)-1-[(3aR,5R,6aR)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl]ethane-1,2-diol 
• 100-52-7 benzaldehyde 
• 321868-59-1 1-[2,2-dimethyl-(3aR,5R,6aR)-perhydrofuro[2,3-d][1,3]dioxol-5-yl]-phenylmethyl-(1RS)-O-(S-methyl dithiocarbonate) 
• 321868-54-6 1-[2,2-dimethyl-(3aR,5R,6aR)-perhydrofuro[2,3-d][1,3]dioxol-5-yl]-phenylmethan-(1RS)-ol 
• 321868-61-5 2,2-dimethyl-5-phenylmethyl-(3aR,5S,6aR)-perhydrofuro[2,3-d][1,3]dioxole 
• 321868-48-8 3-hydroxy-5-phenylmethyl-(3R,5S)-tetrahydrofuran-2-one 
• 14260-67-4 (3aR,5R,6aR)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole-5-carbaldehyde 
• 865487-53-2 methyl (S)-2-acetoxy-4-oxo-5-phenylpentanoate 
• 865487-54-3 methyl (S)-2-hydroxy-4-oxo-5-phenylpentanoate 
• 321868-63-7 3-(4-nitrophenylcarbonyloxy)-5-phenylmethyl-(3S,5S)-tetrahydrofuran-2-one 

Relevant academic research and scientific papers

Stereocontrolled Synthesis of Harzialactone A and Its Three Stereoisomers by Use of Standardized Polyketide Building Blocks

In this paper, we present a short and convenient synthesis of the natural product Harzialactone A and its three stereoisomers. In a three-step synthesis starting from cheap and commercially available benzaldehyde, we created the small polyketidic compound with full control over its two stereogenic centers. To this end, we employed a chiral building block previously described by us, introducing the first stereogenic center through a Horner–Wittig reaction. The second stereogenic center was installed via stereocontrolled syn- or anti-reduction with the corresponding β-hydroxy ketone intermediates. Upon ozonolysis followed by oxidation the natural product and its stereovariants were produced with excellent enantio- and diastereopurities.

Chemoenzymatic asymmetric synthesis of harzia lactone A stereomers

A facile chemoenzymatic synthesis of the harzia lactone A enantiomers was developed. A lipase-catalyzed acylation and an enantio-controlled substrate and reagent-controlled Sharpless' asymmetric dihydroxylation are the key features of the synthesis.

An expeditious route to the antipode of harzialactone a

The antipode of the antitumor marine metabolite harzialactone A was synthesized from l-malic acid via a very efficient route in 40% overall yield involving only two chromatographic separations.

Synthesis of harzialactone A and its isomers from D-glucose and assignment of absolute stereochemistry

The synthesis of the marine metabolite (3R,5R)-harzialactone A 1 from D-glucose is described. Syntheses of all the isomers (3S,5R)-2, (3R,5S)-3 and (3S,5S)-4 of 1 are also described and the absolute stereochemistry for the natural product 1 is assigned un