216753-27-4

Usage

Uses

Used in Pharmaceutical Industry:
(1S,3S,3aR,7aS)-1-ethenyl-1,2,3,3a,7,7a-hexahydro-3-[(3-hydroxy-4-methoxyphenyl)methyl]-7-methylene-4H-inden-4-one is used as a potential pharmaceutical candidate for [application reason]. Its unique structure may contribute to specific biological activities that could be harnessed for therapeutic purposes. Further research is needed to determine its exact applications and efficacy in the pharmaceutical field.
(Note: The specific application reason is not provided in the materials, so it has been left as "[application reason]" to be filled in with accurate information once it is available.)

Upstream product

• 1219637-19-0 (1S,3S,3aR,7aS)-3-[4-methoxy-3-(methoxymethoxy)benzyl]-7-methylene-1-vinyl-1,2,3,3a,7,7a-hexahydro-4H-inden-4-one 
• 623550-62-9 (1S,3S,3aR,4S,7aS)-3-(3-dichloroacetoxy-4-methoxybenzyl)-1,2,3,3a,7,7a-hexahydro-7-methylene-1-(vinyl)inden-4-one 
• 612481-26-2 (1S,3S,3aR,7aS)-3-[[3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4-methoxyphenyl]methyl]-1-ethenyl-2,3,3a,4,7,7a-hexahydro-7-methylene-1H-inden-4-one 

Relevant academic research and scientific papers

Enantioselective total synthesis of otteliones A and B

(Figure Presented) Enantioselective total synthesis of otteliones A and B was accomplished. The key steps are radical cyclization of an alpha-lodoketone to construct the cs-hydrindanone skeleton and Suzuki-Miyaura coupling to incorporate the aromatic group. (+)-Ottelione A was converted to (-)-ottelione B on treatment with NaOH in THF.

Synthesis of the potent anticancer agents ottelione A and ottelione B in both racemic and natural optically pure forms

(Chemical Equation Presented) The powerful antitumor agents ottelione A and B were synthesized in racemic form by a method that relies on selective ring closing metathesis. Optically pure natural (+)-ottelione A was then made from D-ribose, via an α-keto cyclopropane. A key feature of the route is that the cyclopropyl group controls the stereochemistry in the attachment of the ArCH2 unit and is then converted by the action of SmI2 into a vinyl group, so that the substituents on the resulting five-membered ring have the required trans relationship. Epimerization of an intermediate gave access by the same method to the trans ring fused isomer (-)-ottelione B.

Enantioselective total synthesis of (+)-ottelione A, (-)-ottelione B, (+)-3-epi-ottelione A and preliminary evaluation of their antitumor activity

Enantioselective total synthesis of (+)-ottelione A (1) and (-)ottelione B (2), novel and potent antitumor agents from a freshwater plant, and (+)-3-epi-ottelione A (3), the earlier proposed stereostructure of 1, was efficiently achieved starting from the

Synthesis of the otteliones A and B: Use of a cyclopropyl group as both a steric shield and a vinyl equivalent

(Chemical Equation Presented) To A and B: The extremely powerful antitumor agents ottelione A and B have been synthesized from D-ribose. Key steps in the synthesis involve the use of a cyclopropane unit fused onto a five-membered ring to control the stere

Total Synthesis and Absolute Configuration of Otteliones A and B, Novel and Potent Antitumor Agents from a Freshwater Plant

(Matrix presented) The first enantioselective total synthesis of otteliones A and B, biologically important and structurally novel natural products, has been successfully achieved. This total synthesis fully confirms the absolute configuration of these natural products.

Enantioselective total syntheses of (+)- and (-)-ottelione A and (+)- and (-)-ottelione B. Absolute configuration of the novel, biologically active natural products

Following our recent total synthesis of the biologically potent natural products otteliones A and B in racemic form, we have now accomplished the total synthesis of both the enantiomers of otteliones A and B through an enantiodivergent strategy emanating from the readily available Diels-Alder adduct of cyclopentadiene and p-benzoquinone. These endeavors have led to the elucidation of the absolute configuration of naturally occurring otteliones A and B.