117479-71-7

Upstream product

• 123522-72-5 Tributyl-[(E)-2-(2,2-dimethyl-[1,3]dioxan-5-yl)-vinyl]-stannane 
• 131134-38-8 (R)-6-(t-Butyldimethylsiloxymethyl)-3-ethoxy-2,6-dimethyl-2-cyclohexen-1-one 
• 108543-38-0 (-)-cassioside 
• 123522-74-7 (S)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-3-[(E)-2-(2,2-dimethyl-[1,3]dioxan-5-yl)-vinyl]-2,4-dimethyl-cyclohex-2-enone 
• 180692-62-0 (R)-4-(hydroxymethyl)-2,4-dimethyl-3-(1-methylethoxy)-2-cyclohexenone 
• 3973-43-1 4-methylpent-4-enal 
• 102573-86-4 5-ethynyl-2,2-dimethyl-1,3-dioxane 
• 109715-81-3 (2S,3S)-3-hydroxy-2-methylpentanoic acid methyl ester 
• 131134-34-4 (3S,4S)-4-Methyl-7,7-dimethoxy-4-methoxycarbonyl-3-heptanol 
• 131134-36-6 (3S,4R)-4-(t-Butyldimethylsiloxymethyl)-4-methyl-7,7-dimethoxy-3-heptanol 
• 1101871-08-2 C₁₅H₁₈O₂S 
• 131134-37-7 Methyl (R)-4-(t-butyldimethylsiloxymethyl)-4-methyl-5-oxoheptanoate 
• 131134-40-2 (4R)-4-(t-Butyldimethylsiloxymethyl)-4-methyl-7,7-dimethoxy-3-heptanone 
• 131134-35-5 (3S,4R)-4-Hydroxymethyl-4-methyl-7,7-dimethoxy-3-heptanol 

Downstream Products

• 117479-69-3 (4S)-2,4-dimethyl-3-(4-hydroxy-3-hydroxymethyl-butyl)-4-hydroxymethyl-2-cyclohexen-1-one 
• 117479-70-6 (4S)-2,4-dimethyl-3-(3,3-bis-methoxycarbonylpropyl)-4-methoxycarbonyl-2-cyclohexen-1-one 

Relevant academic research and scientific papers

Enantioselective total synthesis of (+)-cassiol

(Chemical Equation Presented) An enantioselective total synthesis of (+)-cassiol is reported. The complex derived from Pd2(pmdba) 3 and enantiopure t-BuPHOX ligand catalyzes enantioconvergent decarboxylative alkylation to generate the quaternary carbon stereocenter at an early stage. The overall synthetic strategy involves a convergent late-stage coupling of two fragments. The synthesis features a longest linear sequence of eight steps.

Detours en route to a total synthesis of (+)-cassiol

A synthesis of the antiulcerogenic compound (+)-cassiol 1b has been achieved in 43% yield starting with lactol (S)-2 and sulfone 26. This short and efficient synthesis features the one-pot Julia olefination reaction of the sodium anion of (S)-2 with 26, through the key intermediate (-)-9. This synthesis has been developed as a result of exploratory experiments including different olefination reactions on 2. An attempt to synthesize the intermediate 9 by an intramolecular aldol condensation approach of the open chain precursor 4 is also described.

A concise synthesis of (+)-cassiol

A synthesis of the anti-ulcerogenic compound (+)-cassiol 1b with 43% overall yield has been achieved. This short and efficient synthesis features the one-pot Julia olefination reaction of lactol (S)-2 with sulfone 3b through the key intermediate (-)-4b.

Cyclohexenone construction by intramolecular alkylidene C-H insertion: Synthesis of (+)-cassiol

We report new procedures for stereoselective cyclopentene and cyclohexenone construction employing the alkylidene carbene C-H insertion reaction. Described are diastereoselective insertion into methylene and enantiospecific insertion into methine C-H bonds. The latter case leads directly to the enantioselective synthesis of (+)-cassiol (1).

An enantioselective total synthesis of (+)-cassiol

An enantioselective total synthesis of (+)-cassiol 1 possessing potent antiulcerogenic activity has been accomplished by using an efficient construction methodology of the asymmetric quaternary carbon center via a highly diastereoselective intramolecular [3+2] dipolar cycloaddition reaction of the nitrile oxide 10 as a key step.

A new catalyst for a Pd catalyzed Alder ene reaction. A total synthesis of (+)-cassiol

The scope of the palladium catalyzed cycloisomerization of enynes in an Alder ene type fashion that led to a new catalytic system was explored in the context of a synthetic strategy to the antiulcerogenic agent (+)-cassiol. In a model study, the effect of

FIRST TOTAL SYNTHESIS OF (+)-CASSIOL. A POTENT ANTIULCEROGENIC COMPOUND

The first total synthesis of (S)-(+)-Cassiol (2) is described.