67765-59-7

Upstream product

• 188107-53-1 (R)-7,7a-Dihydro-benzofuran-2,6-dione 
• 50-99-7 D-glucose 
• 748154-83-8 (diethoxy-phosphoryl)-acetic acid 5-(4-methoxy-benzyloxy)-2-oxo-cyclohex-3-enyl ester 
• 748154-82-7 Bromo-acetic acid (1R,5S)-5-(4-methoxy-benzyloxy)-2-oxo-cyclohex-3-enyl ester 
• 748154-81-6 (4S,6R)-6-Hydroxy-4-(4-methoxy-benzyloxy)-cyclohex-2-enone 
• 70774-92-4 methyl 4,6-O-benzylidene-2-O-p-toluenesulphonyl-α-D-glucopyranoside 
• 3162-96-7 4,6-O-benzylidene-1-O-methyl-α-D-glucopyranoside 
• 72904-78-0 methyl 3-deoxy-4,6-O-phenylmethylene-α-D-arabinohexopyranoside 
• 3150-15-0 methyl 2,3-anhydro-4,6-O-benzilidene-α-D-mannopyranoside 
• 226885-87-6 methyl 4,6-O-benzylidene-3-deoxy-2-O-(4-methoxybenzyl)-α-D-arabinopyranoside 
• 226885-89-8 methyl 3,6-dideoxy-6-iodo-2-O-(4-methoxybenzyl)-4-O-methoxymethyl-α-D-arabinopyranoside 
• 226885-90-1 methyl 3,6-dideoxy-2-O-(4-methoxybenzyl)-4-O-methoxymethyl-α-D-threo-hex-5-enopyranoside 
• 748154-80-5 (2S,4S)-5-Hydroxy-4-(4-methoxy-benzyloxy)-2-methoxymethoxy-cyclohexanone 
• 226885-88-7 methyl 3-deoxy-2-O-(4-methoxybenzyl)-α-D-arabinopyranoside 

Downstream Products

• 1067651-13-1 (6S,7aR)-6-(tert-butyldiphenylsilanyloxy)-7,7a-dihydrobenzofuran-2(6H)-one 

Relevant academic research and scientific papers

Biosynthetically Inspired Syntheses of Secu′amamine A and Fluvirosaones A and B

Presented here is a concise synthesis of secu′amamine A, and fluvirosaones A and B from readily available allosecurinine and viroallosecurinine. The key C2-enamine derivative of (viro)allosecurinine, the presumed biosynthetic precursors of these natural products, was accessed, for the first time, by a VO(acac)2-mediated regioselective Polonovski reaction. Formal hydration and 1,2-amine shift of this pluripotent enamine compound afforded secu′amamine A. Formal oxidative [3+2] cycloaddition reaction between this enamine and TMS-substituted methallyl iodide reagent paved the way to the precursors of fluvirosaones A and B. The relative stereochemistry at the C2 position of these advanced intermediates governs the fate of 1,2-amine shift leading to fluvirosaones A and B. The syntheses of potential biosynthetic precursors and investigations of their chemical reactivities have provided insights regarding the biogenesis of these natural products.

Bio-inspired Total Synthesis of Twelve Securinega Alkaloids: Structural Reassignments of (+)-Virosine B and (?)-Episecurinol A

The so-called Securinega alkaloids constitute a class of tetracyclic biologically active specialised metabolites isolated principally from subtropical plants belonging to the Phyllanthaceae family. Following a strategy based on alternative hypotheses for their biosynthesis, an easy and time-efficient divergent synthesis enabled access to twelve of those alkaloids featuring (neo)(nor)securinane skeletons. Moreover, this work permitted to reassign the absolute configurations of (+)-virosine B and (?)-episecurinol A.

Fluorescence study on the nyctinasty of Phyllanthus urinaria L. using novel fluorescence-labeled probe compounds

We report the synthesis of fluorescence-labeled probes based on phyllanthurinolactone 1, which is a leaf-closing substance of Phyllanthus urinaria L. The fluorescence study using biologically active probe 2 and inactive probes (epi-2 and 31) revealed that

Enantioselective synthesis of phyllanthurinolactone, a leaf-closing substance of Phyllanthus urinaria L., and its analogs toward the development of molecular probes

We report enantioselective synthesis of phyllanthurinolactone (1), a leaf-closing substance of Phyllanthus urinaria L., and its analogs with sugars other than D-glucose. Structure-activity relationship study using them revealed that the structure of the sugar moiety did not affect their bioactivity at all. This result is very important for the development of molecular probes based on the structure of 1.

From p-benzoquinone to cyclohexane chirons: First asymmetric synthesis of (+)-rengyolone and (+)- and (-)-menisdaurilide

Starting from a common, easily available, enantiopure monoketal of p-benzoquinone, the synthesis of a large number of cyclohexane chirons has been achieved. The first synthesis of (+)-rengyolone and (+)- and (-)-menisdaurilide has been performed from one of these new building blocks. The wide variety of functional groups of this series of chirons makes them useful for subsequent synthetic processes.

First synthesis of (+)-rengyolone and (+)- and (-)-menisdaurilide

The benzofuranone natural products (+)-rengyolone and (+)- and (-)-menisdaurilide have been synthesised for the first time from a common enantiopure cyclohexane building block derived from a monoketal of p-benzoquinone.