68225-44-5

Upstream product

• 1779-49-3 Methyltriphenylphosphonium bromide 
• 68225-42-3 2-[(1S,2S)-2-acetyl-1-methylcyclobutyl]acetic acid 
• 53171-63-4 (+/-)-3-oximino-1,4,4-trimethylbicyclo<3.2.0>heptane 
• 19493-09-5 Methylenetriphenylphosphorane 
• 105539-65-9 (1S,6S)-5,5-(ethylenedioxy)bicyclo<4.2.0>octane-1-carboxamide 
• 105539-60-4 (1S,6S)-5,5-(ethylenedioxy)bicyclo<4.2.0>octane-1-carboxylic acid 
• 105539-64-8 (1S,6S)-5,5-(ethylenedioxy)-N-((S)-1-phenylethyl)bicyclo<4.2.0>octane-1-carboxamide 
• 105539-62-6 (1RS,6RS)-5-oxobicyclo<4.2.0>octane-1-carbonyl chloride 
• 24079-80-9 (1RS,6RS)-5-oxobicyclo<4.2.0>octane-1-carboxylic acid 
• 105539-58-0 methyl (1RS,6RS)-5-oxobicyclo<4.2.0>octane-1-carboxylate 
• 105539-63-7 (1RS,6RS)-5-oxo-N-((S)-1-phenylethyl)bicyclo<4.2.0>octane-1-carboxamide 
• 105616-26-0 (1S,6S)-6-methylbicyclo<4.2.0>oct-3-en-2-ol 
• 105616-24-8 (1S,6R)-6-methylbicyclo<4.2.0>octan-2-one 
• 39493-57-7 (1R,6S)-5,5-(ethylenedioxy)-1-methylbicyclo<4.2.0>octane 

Downstream Products

• 26532-22-9 grandisol 

Relevant academic research and scientific papers

Enantioselective Intermolecular [2+2] Photocycloaddition Reaction of Cyclic Enones and Its Application in a Synthesis of (-)-Grandisol

The intermolecular [2+2] photocycloaddition of typical cyclic α,β-unsaturated enones, such as 2-cyclohexenone, with olefins was performed in moderate to good yields (42-82%) and with high enantioselectivity (82%-96% ee). An unusual substitution pattern at the chiral oxazaborolidine-AlBr3 Lewis acid complex that promotes the reaction was found to be crucial for the success of the reaction. The method was applied to the enantioselective synthesis of the monoterpene (-)-grandisol, which could be accomplished in six steps and with an overall yield of 13% starting from 3-methyl-2-cyclohexenone.

Utilization of Selenium-directed Cycloadditions: Concise Synthesis of (+/-)-Fragranol

The reaction of 2-(phenylseleno)prop-1-ene 1 and methyl vinyl ketone 2 in the presence of EtAlCl2 gave the cycloadducts 3a and 3b.A radical substitution of the adducts 3a and 3b with allyltributyltin gave the allylated cyclobutane product, which was transformed into the cyclobutane natural product, (+/-)-fragranol.Stereoselective radical substitution using the ethylene glycol ketals of compounds 3a and 3b was also achieved.

Practical Preparation of Bicyclohept-3-en-6-ones and its Utilisation in Stereoselective Total Synthesis of Grandisol and Lineatin via a Versatile Intermediate.

New and efficient stereoselective total syntheses have been devised for racemic grandisol and lineatin, two important components of pheromonic blends.They are based on the utilisation of 1,4-dimethylbicyclohept-3-en-6-one as a pivotal intermediate.This compound, as well as other bicyclohept-3-en-6-ones, are now easily available by a practical bicyclization of the corresponding 3-hydroxy-6-alkenoic acids.

STEREOSELECTIVE TOTAL SYNTHESIS OF RACEMIC GRANDISOL via 3-OXIMINO-1,4,4-TRIMETHYLBICYCLOHEPTANE. AN IMPROVED PRACTICAL PROCEDURE.

(+/-)Grandisol was stereoselectively obtained via 1,4,4-trimethylbicycloheptane-3-one and its oxime by an improved procedure. 2,5,5-trimethylhept-1,6-dien-4-ol, the open chain molecule, was synthesized by two routes.Its conversion into (+/-)grandisol was performed emploing the photobicyclization as key step.

Synthesis of Optically Pure Enantiomers of Grandisol

The synthesis of both enantiomers of grandisol (1 and 1') of greater than 99percent optical purity is described.The key step is the separation of diastereomeric amides 11 and 12 and subsequent cleavage to give optically pure acids 8 and 8'.Since 8 and 8' contain a quaternary chiral center, the optical purity of derived grandisol 1 and 1' is ensured.

STEREOSELECTIVE TOTAL SYNTHESIS OF RACEMIC GRANDISOL. AN IMPROVED CONVENIENT PROCEDURE

(+/-) Grandisol has been stereoselectively synthesized in a 31 percent overall yield by a practical and convenient procedure employing the Salomon photobicyclization as the key-step.