188567-98-8

Upstream product

• 917-54-4 methyllithium 
• 188568-04-9 (3R)-3-(2,2-dimethoxyethyl)-4-methyl-4-pentenoic acid 
• 872525-75-2 (R)-4-(2,2-Dimethoxy-ethyl)-5-methyl-hex-5-en-2-one 
• 139561-13-0 (R)-methyl 3-(2,2-dimethoxyethyl)-4-methylpent-4-enoate 
• 731811-36-2 (R)-4-Methyl-3-(2-oxo-ethyl)-pent-4-enoic acid 

Downstream Products

• 859843-12-2 (5R)-2-hydroxymethyl-5-isopropenyl-cyclohex-2-enone 
• 872525-97-8 (R)-4-Isopropenyl-6-oxo-cyclohex-1-enecarbaldehyde 
• 872525-82-1 (4S,4aS,7R,8aR)-4-{(R)-1-Acetoxy-2-[(1R,2S)-2-(tert-butyl-diphenyl-silanyloxymethyl)-1-methyl-5-oxo-cyclopentyl]-ethyl}-4a-formyl-2-hydroxy-7-isopropenyl-5-oxo-3,4,4a,5,6,7,8,8a-octahydro-naphthalene-1-carboxylic acid allyl ester 
• 731811-35-1 (+)-5-isopropenyl-3-methyl-cyclohex-2-enone 
• 188567-99-9 (R)-desmethylcarvone 

Relevant academic research and scientific papers

Studies towards the total synthesis of ouabagenin

An anionic cyclization strategy developed in our laboratory was used to produce a versatile and convergent synthesis of an advanced tetracyclic intermediate for the construction of ouabagenin and closely related analogs.

Synthesis of (+)- and (-)-isocarvone

The first synthesis of 5-isopropenyl-3-methyl-cyclohex-2-enone, (isocarvone) (2), in enantiomerically pure form is reported. Both enantiomers of 2 can be produced by manipulation of carboxylic acid 5, which is available from R-(-)-carvone (1). These materials provide new chiral building blocks that could be used in total synthesis of natural products and related optically active compounds.

A stereoselective total synthesis of (-)-rishitin

A new synthesis of (-)-rishitin (1) is reported, starting with chiral pool molecules. The crucial step is a stereoselective vinyl radical cyclization, which gives a 10:1 ratio of 21 to 22.