41678-32-4

Upstream product

• 13720-37-1 dihydro-α-ionol 
• 6267-39-6 3-ethoxy-5,5-dimethyl-2-cyclohexen-1-one 
• 147379-75-7 (E)-1-(phenylsulfonyl)-4-<(R)-2,6,6-trimethyl-2-cyclohexenyl>-1-butene 
• 347852-13-5 7,8-dihydro-α-ionol 
• 13720-37-1 dihyro-α-ionol 
• 14554-14-4 (1R,1'RS)-1-methyl-3-(2',6',6'-trimethyl-2'-cyclohexenyl)propyl p-toluenesulfonate 
• 137937-65-6 (1R,1'R*,2'R*,3'R*)-3-(2',3'-dihydroxy-2',6',6'-trimethyl-2'-cyclohexenyl)-1-methylpropyl p-toluenesulfonate 
• 137937-64-5 (1R,1'R*,2'R*,3'S*)-3-(2',3'-epoxy-2',6',6'-trimethyl-2'-cyclohexenyl)-1-methylpropyl p-toluenesulfonate 
• 3293-45-6 (2R,1'RS)-4-(2',6',6'-trimethyl-2'-cyclohexenyl)but-2-yl acetate 
• 127-41-3 alpha-ionone 
• 147379-80-4 (1R,3R,6R,10R)-3-(phenylsulfonyl)-1,7,7-trimethyl-2-oxabicyclo<4.4.0>decan-10-ol 
• 147379-77-9 (E)-4-<(1R,2R,3R)-2,3-dihydroxy-2,6,6-trimethylcyclohexyl>-1-(phenylsulfonyl)-1-butene 
• 147379-76-8 (E)-4-<(1R,2R,3S)-2,3-epoxy-2,6,6-trimethylcyclohexyl>-1-(phenylsulfonyl)-1-butene 
• 147379-73-5 (3)-<(R)-2,6,6-trimethl-2-cyclohexenyl>propanal 

Relevant academic research and scientific papers

Chiral syntheses of edulans I, II and dihydroedulans I, II and absolute cenfigurations of edulans I, II

Enantiospecific syntheses of (+)- and (-)-edulans I, II and (-)-dihydroedulans I, II, starting from (R)- and (S)-3-hydroxybutyric acid methyl esters, allowed the determination of the absolute configurations of edulans I, II.

Pheromone Synthesis, CXLVII. Synthesis of (1R,3S,6R,9S,10S)-9,10-Epoxytetrahydroedulan, the Main Component of the Hairpencil Secretion of Male Danaid Butterfly Eupoloea klugii

The natural and (+)-enantiomer of 9,10-epoxytetrahydroedulan decane>, the main component of the hairpencil secretion of Euploea klugii, was synthesized via (-)-dihydroedulan II (2) by starting from (S)-2,4,4-trimethyl-2-cyclohexen-1-ol (D). Key Words: Danaid butterfly / Edulan II derivatives / Euploea klugii / Pheromones

A Synthetic Study of (-)-Dihydroedulan II and Related Compounds

(-)-Dihydroedulan II and related compounds were synthesized from (2R,1'RS)-dihydro-α-ionol, which was prepared by lipase-catalyzed enantioselective transesterification of the corresponding diastereomeric mixture as the key-step.Fungal allylic oxidation of (-)-dihydroedulan II worked well to afford a corresponding alcohol as well as (+)-dihydroedulan-8-one.

Epoxytetrahydroedulan, a New Terpenoid from the Hairpencils of Euploea (Lep.: Danainae) Butterflies

The main component among the volatiles from hairpencils of male danaid butterflies of the genus Euploea was found to be 9,10-epoxytetrahydroedulan: (1R,2S,4S,7R,10S)-1,6,6,10-tetramethyl-3,11-dioxatricyclo2.4>undecane (12).Identification and synthesis of the compound are described.Another edulan derivative, (1R*,3S*,6R*)-1,3,7,7-tetramethyl-2-oxabicyclodec-9-en-8-one (13) could be identified from the hairpencils of Danaus plexippus males.

A NOVEL SELENIUM-MEDIATED SPIROANNELATION: ONE-STEP PREPARATION OF d1-THEASPIRANE FROM α-DIHYDROIONOL

dl-Theaspirane (1) was prepared by the selenium-mediated electrochemical oxidation of α-dihydroionol (2), via a novel selenium-mediated spiroannelation.

New Syntheses of Edulans and Theaspiranes from α-Inone

New syntheses of edulans and theaspiranes are described.The key step involves the cyclization of 4-(2',6',6'-trimethyl-2'-hydroxy-3'-cyclohexen-1'-yl)-butan-2-ol (7) and 4-(2',6',6'-trimethyl-1',2'-dihydroxy-3'-cyclohexen-1'-yl)-butan-2-ol (8) derived from α-ionone.The diol (7) and triol (8) were cyclized with acetic acid into the corresponding tetrahydropyran derivatives ; the latter two compounds were dehydrated to edulan I and II (13a, 13b).On treatment with tosyl chloride in pyridine, however, triol (8) gave spiro-compounds (11a, 11b and 12); (11a and 11b) were easily converted to cis- and trans-theaspirone by oxidation and 5,6-erythro-6-hydroxy-dihydrotheaspiranes (15a and 15b) by reduction.