211503-65-0

Upstream product

• 211503-63-8 (4S,5R,)-(-)-5-Isopropenyl-2,3,4-trimethylcyclohex-2-enone 
• 211503-61-6 (1S,4S,5R,)-(-)-5-Isopropenyl-2,3,4-trimethylcyclohex-2-enol 
• 211503-64-9 ((1R,5R,6S)-5-Isopropenyl-1,2,6-trimethyl-cyclohex-2-enyl)-acetic acid ethyl ester 
• 211503-60-5 (3R,2S,5R)-(+)-5-Isopropenyl-2,3,4-trimethylcyclohexene-3-acetic acid 
• 1117-96-0 Diazoethan 

Relevant academic research and scientific papers

An enantiospecific approach to pinguisanes from (R)-carvone. Total synthesis of (+)-pinguisenol

Enantiospecific total synthesis of (+)-pinguisenol 1, a sesquiterpene containing a cis-1,2,6,7-tetramethylbicyclo[4.3.0]nonane carbon framework incorporating two vicinal quaternary carbon atoms and four cis-oriented methyl groups on four contiguous carbon atoms, isolated from a liverwort, is described. The orthoester Claisen rearrangement of the allyl alcohol 9, obtained from (R)-carvone, generates the ester 12. Intramolecular cyclopropanation of the diazo ketone 13, derived from the ester 12, furnishes the tricyclic ketone 7. Degradation of the isopropenyl group followed by regioselective reductive cyclopropane ring cleavage transforms compound 7 into the hydroxy ketone 21. Wblff-Kishner reduction of the hydroxy ketone 21 followed by oxidation and Grignard reaction furnishes pinguisenol (+)-1. The Royal Society of Chemistry 2000.

Enantiospecific synthesis of (+)-pinguisenol, (+)-pinguisen-10-one and (-)-pinguisen-8,10-dione

The first enantiospecific total synthesis of the sesquiterpene (+)- pinguisenol, the optical antipode of the natural product, and the analogues (-)-pinguisen-10-one and (+)pinguisen-8,10-dione, starting from R-carvone are described.