70855-67-3

Upstream product

• 541-50-4 2-acetoacetic acid 
• 89-82-7 pulegone 
• 10191-25-0 3-oxo-valeric acid 
• 869991-51-5 Acetic acid (R)-4,4,7-trimethyl-1,2,3,4,5,6,7,8-octahydro-naphthalen-2-yl ester 
• 869944-56-9 (R)-4,4,7-Trimethyl-1,2,3,4,5,6,7,8-octahydro-naphthalen-2-ol 
• 869944-53-6 (7R)-2-chloro-4,4,7-trimethyl-1,2,3,4,5,6,7,8-octahydronaphthalene 
• 33557-42-5 (+)-(1S,5R)-1-(2-propen-1-yl)-2-(1-methylethylidene)-5-methylcyclohexanol 
• 125159-09-3 (R)-4,4,7-trimethyl-1,4,5,6,7,8-hexahydro-2(3H)-naphthalenone 

Relevant academic research and scientific papers

Copper(II)-Catalyzed Tandem Decarboxylative Michael/Aldol Reactions Leading to the Formation of Functionalized Cyclohexenones

This work describes the development of a new single-pot copper(II)-catalyzed decarboxylative Michael reaction between β-keto acids and enones, followed by in situ aldolization, which results in highly functionalized chiral and achiral cyclohexenones. The achiral version of this Robinson annulation features a hitherto unprecedented Michael reaction of β-keto acids with sterically hindered β,β′-substituted enones and provides access to all carbon quaternary stereocenter-containing cyclohexenones (11 examples, 43-83% yield). In addition, an asymmetric chiral bis(oxazoline) copper(II)-catalyzed single-pot Robinson annulation has been devised for preparing chiral cyclohexenones, including some products that contain vicinal stereocenters (5 examples, 65-85% yield, 84-94% ee). This latter protocol has been successfully applied to the enantioselective formation of the oxygenated 10-nor-steroid core from readily available starting materials.

CYCLIZATION OF 1,5-HEXADIEN-3-OLS. OBTENTION OF CHLORO-OCTALINES, OCTALONES AND HEXAHYDRO-AZULENONES FROM ALLYL-PULEGOLS

The TiCl4 mediated cyclization of allyl-pulegols gives chlorooctalines (1,5-hexadien-3-ol system is cyclized into 4-chlorocyclohexene moiety).From chloro-octalines, octalones and hexahydro-azulenones are obtained respectively into three and two steps.