473791-23-0

Upstream product

• 473791-50-3 Acetic acid (2R,3R,4aS,8R,8aS)-8-(tert-butyl-dimethyl-silanyloxy)-2,3-dimethoxy-2,3-dimethyl-5-oxo-2,3,4a,5,8,8a-hexahydro-benzo[1,4]dioxin-6-ylmethyl ester 
• 1350450-07-5 C₂₁H₃₆O₈Si 
• 1219090-28-4 C₂₁H₃₈O₈Si 
• 1219090-31-9 C₁₉H₃₆O₇Si 
• 1219090-30-8 C₂₂H₄₀O₇Si 
• 1039643-44-1 5,5a-didehydro-2,3-O-[(2R,3R)-2,3-dimethoxybutane-2,3-diyl]-4,6-O-isopropylidene-5a-carba-β-D-xylohexopyranose 
• 473791-28-5 ((2R,3R,4aS,5R,8aR)-7-Benzenesulfinylmethyl-2,3-dimethoxy-2,3-dimethyl-2,3,4a,5,8,8a-hexahydro-benzo[1,4]dioxin-5-yloxy)-tert-butyl-dimethyl-silane 
• 473791-36-5 (2R,3R,4aS,7S,8R,8aS)-8-(tert-Butyl-dimethyl-silanyloxy)-2,3-dimethoxy-7-methoxymethoxy-2,3-dimethyl-6-methylene-hexahydro-benzo[1,4]dioxin-5-one 
• 473791-32-1 tert-Butyl-((2R,3R,4aS,5R,6S,8aR)-2,3-dimethoxy-6-methoxymethoxy-2,3-dimethyl-7-methylene-octahydro-benzo[1,4]dioxin-5-yloxy)-dimethyl-silane 
• 473791-30-9 (2R,3R,4aS,5R,6S,8aR)-5-(tert-Butyl-dimethyl-silanyloxy)-2,3-dimethoxy-2,3-dimethyl-7-methylene-octahydro-benzo[1,4]dioxin-6-ol 
• 1204745-24-3 (4S,5R,6R)-2-acetoxymethyl-4-O-tert-butyldimethylsilyl-5,6-[(2R,3R)-2,3-dimethoxybutan-2,3-dioxy]-2-cyclohexen-1-one 

Relevant academic research and scientific papers

Filling Some Blanks in a Divergent Approach to Gabosines: Enantioselective Synthesis of (–)-Epiepoxydon, (+)-Phyllostine, (–)-Gabosine D, and (–)-Gabosine E

The levorotatory enantiomers of gabosines D and E were synthesized through a divergent approach that could equally well be applied to the synthesis of the dextrorotatory enantiomers, which have been isolated from natural sources. The approach relies on an initial desymmetrization of p-methoxyphenol, followed by an enzymatic resolution that separately provides the two enantiomers of synthon 3. This versatile synthon can be further transformed into the diverse polyoxygenated cyclohexane target molecules. Key steps in the synthesis of (–)-gabosines D and E from (4R,6S)-3 are the stereoselective hydroxymethylation at the α-carbonyl position leading to (+)-4, and the subsequent reagent-controlled epoxidation of the carbon–carbon double bond. A branching in the sequence also allowed the synthesis of the anhydrogabosines (–)-epiepoxydon and (+)-phyllostine.

Inhibition of glutathione S-Transferase M1 by new gabosine analogues is essential for overcoming cisplatin resistance in lung cancer cells

A new class of human GST inhibitors has been identified via rational design approach; we report their discovery, synthesis, inhibitory activity, and synergetic effect in combination with cisplatin against A549 lung cancer cell line. The results of this ef

Facile syntheses of (+)-gabosines A, D, and e

(+)-Gabosines A (12), D (4), and E (5), which share the same trihydroxycyclohexenone skeleton, were synthesized from enone 11 as the common intermediate. The key building block 11 was accessed by an intramolecular aldol cyclization of a diketone derived f

Syntheses of gabosine A, B, D, and E from allyl sulfide derived from (-)-quinic acid

An efficient conversion of allyl sulfide 6 prepared from (-)-quinic acid (5) to gabosines was achieved by a series of sequential reactions: i) Mislow-Evans rearrangement, ii) SeO2 oxidation, iii) conjugate addition of sodium hydroxide or sodium