98751-78-1

Usage

Uses

Used in Pharmaceutical Research:
(3aR,6S,7aR)-3a,6,7,7a-Tetrahydro-6-hydroxy-6-methyl-3-methylene-2,5(3H,4H)-benzofurandione is used as a key intermediate in pharmaceutical research for the development of new drugs. Its unique structure and chirality offer opportunities for the synthesis of novel compounds with potential therapeutic applications.
Used in Organic Synthesis:
In the field of organic synthesis, (3aR,6S,7aR)-3a,7,7a-Tetrahydro-6-hydroxy-6-methyl-3-methylene-2,5(3H,4H)-benzofurandione serves as a versatile building block for the creation of various organic compounds. Its furandione core and functional groups can be further modified to generate a wide range of molecules with different properties and applications.
Used in Drug Discovery:
As a benzofurandione derivative, (3aR,6S,7aR)-3a,6,7,7a-Tetrahydro-6-hydroxy-6-methyl-3-methylene-2,5(3H,4H)-benzofurandione is utilized in drug discovery for the identification and optimization of bioactive molecules. Its unique structure and potential biological activity make it a promising candidate for the development of new therapeutic agents.
Used in Chiral Chemistry:
The chirality of (3aR,6S,7aR)-3a,6,7,7a-Tetrahydro-6-hydroxy-6-methyl-3-methylene-2,5(3H,4H)-benzofurandione makes it an important compound in chiral chemistry. It can be used to study the effects of stereochemistry on the properties and reactivity of molecules, as well as to develop enantioselective synthetic methods and asymmetric catalysts.

Upstream product

• 124618-18-4 (3aR,5R,6S,7aR)-5,6-Dihydroxy-6-methyl-3-methylene-hexahydro-benzofuran-2-one 
• 99-48-9 (4R,6R)-carveol 
• 124618-14-0 (3aS,4aR,7aR,8aR)-2,3a,7-Trimethyl-hexahydro-furo[2',3':4,5]benzo[1,2-d][1,3]dioxol-6-one 
• 24120-79-4 (1R,2R,4S,6S)-(-)-1-methyl-4-(prop-1-en-2-yl)-7-oxabicyclo[4.1.0]heptan-2-ol 
• 1170967-38-0 (3aR,5S,6S,7aR)-5,6-dihydroxy-6-methyl-3-methylenehexahydrobenzofuran-2(3H)-one 
• 133076-83-2 (3aS,4aR,7S,7aR,8aR)-7-Hydroxymethyl-2,2,3a-trimethyl-hexahydro-furo[2',3':4,5]benzo[1,2-d][1,3]dioxol-6-one 
• 7086-66-0 2-<(1RS)-4-methylcyclohex-3-enyl>acetic acid 
• 124618-18-4 (3aS,5S,6R,7aS)-5,6-Dihydroxy-6-methyl-3-methylene-hexahydro-benzofuran-2-one 
• 50-00-0 formaldehyd 
• 1091593-78-0 (1R,5S)-(+)-5-hydroxy-5-methyl-4-oxocyclohex-2-enyl (diethoxyphosphoryl)acetate 
• 139685-63-5 (3aS,4aR,7aR,8aR)-2,2,3a-Trimethyl-7-methylene-hexahydro-furo[2',3':4,5]benzo[1,2-d][1,3]dioxol-6-one 
• 139618-31-8 (3aR,5S,7aS)-2,2,7a-Trimethyl-5-(2-methyl-oxiranyl)-3a,4,5,7a-tetrahydro-benzo[1,3]dioxole 
• 124618-13-9 (3aR,4R,4aS,7aR,8aR)-4-Iodo-3a,7-dimethyl-2-trichloromethyl-hexahydro-furo[2',3':4,5]benzo[1,2-d][1,3]dioxol-6-one 

Relevant academic research and scientific papers

Diastereoselective SmI2 mediated cascade radical cyclisations of methylenecyclopropane derivatives - Syntheses of paeonilactone B and 6-epi-paeonilactone A

The SmI2 mediated cascade cyclisations of several methylenecyclopropyl ketones have been examined and found to proceed with high diastereoselectivity, which is critically dependent on the presence of HMPA in the reaction. In one case the radica

Diastereoselective SmI2-mediated cascade radical cyclisations of methylenecyclopropane derivatives - A synthesis of paeonilactone B

The SmI2-mediated cascade reaction of methylenecyclopropyl ketone 9 proceeds with high diastereoselectivity, which is critically dependent on the presence of HMPA, and provides a short route to paeonilactone B.

Total Synthesis of (+)-Paeonilactone B and (-)-Paeonisuffrone

A novel synthesis of (+)-paeonilactone B, a minor constituent of Paeoniae Radix, and the first synthesis of (-)-paeonisuffrone, a new monoterpene recently isolated from Moutan Cortex, have been accomplished from the tricyclic compound which funcioned well

New stereoselective synthesis of paeonilactone B

A new stereoselective synthesis of paeonilactone B has been achieved in ten steps and in 11.5% overall yield starting from the enantiomerically enriched terpenol 2. Key synthetic steps are based on a regioselective metalation and on a regio- and diastereo

The telescoped intramolecular Michael/olefination (TIMO) approach to α-alkylidene-γ-butyrolactones: Synthesis of (+)-paeonilactone B

(Chemical Equation Presented) Scoping out TIMO: A telescoped intramolecular Michael addition/proton transfer/ Horner-Wadsworth-Emmons olefination sequence was developed to provide rapid access to α-alkylidene-γ- butyrolactones (see scheme). The method was applied to prepare a range of tetrahydrobenzofuran-2,5-diones and related systems, and it was utilized in a short synthesis of enantiomerically pure (+)-paeonilactone B.

The preparation of α-alkylidene-γ-butyrolactones using a telescoped intramolecular Michael/Olefination (TIMO) sequence: Synthesis of (+)-paeonilactone B

A novel telescoped intramolecular Michael addition/proton transfer/HWE olefination sequence has been developed to provide rapid access to α-alkylidene-γ-butyrolactones. This methodology has been applied to prepare a range of tetrahydrobenzofuran-2,5-diones, and related systems, and also utilised in an extremely short synthesis of the natural product (+)-paeonilactone B in enantiomerically pure form. In addition, preliminary experiments are described that illustrate a palladium-catalysed variant proceeding by way of a π-allyl intermediate. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.

Enantiospecific syntheses of paeonilactone A, paeonilactone B, 7S-paeonimetabolin-I, and 7R-paeonimetabolin-I from R-(-)-carvone

The first enantiospecific syntheses of the title monoterpenes have been accomplished starting with R-(-)-carvone, which made their absolute structures unequivocal.

STEREOSELECTIVE SYNTHESIS OF THE PAEONILACTONES A, B AND C

The first total syntheses of the title monoterpenes are reported.