17063-17-1

Upstream product

• 83999-47-7 2-Acetoxy-2,6,6-trimethyl-3-cyclohexen-1-one 
• 83999-46-6 2-Hydroxy-2,6,6-trimethyl-cyclohex-3-enone 
• 147641-90-5 (3aS,7S,7aS)-7-iodo-4,4,7a-trimethyl-3a,4,5,6,7,7a-hexahydrobenzofuran-2(3H)-one 
• 147730-51-6 (3aS,7aR)-4,4,7a-trimethyl-3a,4,5,7a-tetrahydrobenzofuran-2(3H)-one 
• 147641-89-2 (S)-(2,6,6-trimethylcyclohex-2-enyl)acetic acid 
• 143658-43-9 ethyl <2,6,6-trimethyl-2-cyclohexenyl>acetate 
• 134780-16-8 (R)-2,4,4-trimethyl-2-cyclohexen-1-ol 
• 199727-73-6 (1R,3S,4S)-5,8,8-Trimethyl-2-oxa-bicyclo[2.2.2]oct-5-ene-3-carboxylic acid ethyl ester 
• 199727-74-7 (3S,3aR,7aR)-3-Hydroxy-4,4,7a-trimethyl-3a,4,5,7a-tetrahydro-3H-benzofuran-2-one 
• 41169-33-9 3,5,5-trimethylcyclohexa-1,3-diene 
• 199727-75-8 Toluene-4-sulfonic acid (3S,3aR,7aR)-4,4,7a-trimethyl-2-oxo-2,3,3a,4,5,7a-hexahydro-benzofuran-3-yl ester 
• 83999-48-8 (3aS,7aR)-3a-Hydroxy-4,4,7a-trimethyl-3a,4,5,7a-tetrahydro-3H-benzofuran-2-one 

Downstream Products

• 147730-52-7 (+)-epiloliolide 
• 1133-03-5 Loliolide 

Relevant academic research and scientific papers

Total Synthesis of (R)-Dihydroactinidiolide and (R)-Actinidiolide Using Asymmetric Catalytic Hetero-Diels-Alder Methodology

The total synthesis of the naturally occurring bicyclic lactones (R)-dihydroactinidiolide and (R)-actinidiolide is presented. The key step in the syntheses is the copper(II)-bisoxazoline-catalyzed hetero-Diels-Alder reaction of a cyclic diene with ethyl glyoxylate giving the hetero-Diels-Alder product in high yield and with very high regio-, diastereo-, and enantioselectivity. The total syntheses proceed via an intermediate, which also has the potential for a series of other natural products. The structure of the key intermediate is confirmed by X-ray analysis.

Carotenoids and Degraded Carotenoids, VIII. Synthesis of (+)-Dihydroactinidiolide, (+)- and (-)-Actinidiolide, (+)- and (-)-Loliolide as well as (+)- and (-)-Epiloliolide

Enantiomerically pure (S)-2,4,4-trimethyl-2-cyclohexen-1-ol (1) was efficiently converted into four degraded lactonic carotenoids: (S)-dihydroactinidiolide (5), (S)-actinidiolide (9), (6S,7aR)-loliolide (11) and (6S,7aS)-epiloliolide (12). (R)-Actinidioli

Oxidation of Enol Silyl Ethers: Preparation of Aeginetolide, Dihydroactinidiolide, and Actinidiolide

The preparation of the C11-terpenic lactones aeginetolide (1), dihydroactinidiolide (2), and actinidiolide (3) by using 1,3,3-trimethyl-2-(trimethylsiloxy)cyclohexene (9) as a common precursor is discussed.The key steps in the synthetic route involve the sequential m-chloroperbenzoic acid (MCPBA) oxidation and acetylation of 9 and of the siloxy diene 13 derived from 9.