67772-77-4

Usage

InChI:InChI=1/C7H8O3/c1-3-2-4(8)6-7(10-6)5(3)9/h2,4,6-8H,1H3/t4-,6+,7-/m0/s1

Upstream product

• 162809-82-7 (+)-(2R,3S,4S)-4-tert-butyldimethylsilyloxy-2,3-epoxy-6-methyl-1-cyclohex-5-en-1-one 
• 851129-88-9 (1S,2R,3R,4S)-2,3-epoxy-6-methyl-1-[(p-tolylsulfonyl)methyl]cyclohex-5-ene-1,4-diol 
• 697741-20-1 (4S)-4-(tert-butyldimethylsilyloxy)-10-phenylthiocyclohex-2-enone 
• 1289117-14-1 (+)-(1R,3R,5S,6S)-5-(tert-butyldimethylsilyloxy)-3-methyl-3-(phenylthio)-7-oxabicyclo[4.1.0]heptan-2-one 
• 887404-60-6 (4S,6R)-4-(tert-butyldimethylsilyloxy)-6-methyl-6-phenylthiocyclohex-2-enone 
• 162809-81-6 [1aR-(1aα,2aβ,3β,6β,6aβ,7α,7aα)]-3a-methyl-7-{[(1,1-dimethylethyl)dimethylsiyl]oxy}-2a,3,6,6a,7,7a-hexahydro-[3,6]methanonaphth[2,3-b]oxiren-2(1aH)-one 
• 162809-80-5 [1aR-(1a,2aβ,3β,6β,6aβ,7α,7aα)]-7-{[(1,1-dimethylethyl)dimethylsiyl]oxy}-2a,3,6,6a,7,7a-hexahydro[3,6]methanonaphth[2,3-b]oxiren-2(1aH)-one 
• 313547-95-4 (3R,4R,5R)-3-[(tert-butyl-dimethylsilyl)oxy]-4,5-(isopropylidenedioxy)-1-cyclohexanone 
• 74293-60-0 (3aR,7R,7aS)-7-hydroxy-2,2-dimethyltetrahydrobenzo[d][1,3]dioxol-5(6H)-one 
• 188308-06-7 (2R,3S,4S)-4-[(tert-Butyldimethylsilyl)oxy]-2,3-epoxy-6-iodo-5-cyclohexen-1-one 
• 188308-05-6 (2R,3S,4S)-4-[(tert-Butyldimethylsilyl)oxy]-2,3-epoxy-5-cyclohexen-1-one 
• 394250-86-3 (1R,5S,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxymethyl-7-oxa-bicyclo[4.1.0]heptan-2-one 
• 394250-87-4 (-)-(2R,3S,4S)-4-tert-butyldimethylsilyloxy-2,3-epoxy-6-methylene-1-cyclohexanone 
• 532989-52-9 (1R,5S,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-3-methyl-3-phenylselanyl-7-oxa-bicyclo[4.1.0]heptan-2-one 

Downstream Products

• 1204745-26-5 (+)-gabosine A 
• 15254-70-3 (1R,6S)-3-methyl-7-oxabicyclo[4.1.0]hept-3-ene-2,5-dione 
• 1043454-68-7 (2R,4S,5R)-4,5-dihydroxy-2-methylcyclohexan-1-one 

Relevant academic research and scientific papers

Synthesis of (+)-epiepoformin using the base-catalyzed Diels-Alder reaction of 3-hydroxy-2-pyrone

Asymmetric total synthesis of (+)-epiepoformin was achieved in short steps using the base-catalyzed asymmetric Diels-Alder (DA) reaction of 3-hydroxy-2-pyrone with chiral acrylate. Since the synthesis produced Ogasawara's intermediate, it is also presented as a formal synthesis of (-)-theobroxide.

The enantiodivergent total synthesis of natural and unnatural enantiomers of theobroxide

Both enantiomers of theobroxide, a potato micro-tuber inducing substance isolated from Lasiodiplodia theobromae, have been synthesized from a common chiral building block serving as a chiral equivalent of 1,4-dihydroxy-2,5-cyclohexadiene. The synthesis has verified the proposed structure and the absolute configuration.

Divergent approach to gabosines and anhydrogabosines: Enantioselective syntheses of (+)-epiepoformin, (+)-EpoKformin, (+)-gabosine A, and gabosines B and F

A divergent approach to polyoxygenated methylcyclohexanes has been applied to synthesize several gabosines and anhydrogabosines. The starting hydroxycyclohexenone, which is readily available in any antipodal form, provides access to both enantiomers of the target compounds. The syntheses of anhydrogabosines involve three main transformations: α-methylation, epoxidation, and sulfur removal, whereas the syntheses of gabosines require an additional epoxide hydrolysis step. The strategy has been applied to the synthesis of (+)-epiepoformin, (+)-epoformin, (+)-gabosine A, and gabosines B and F, through straightforward sequences in good overall yields. A cyclohexenone that is easily available in any antipodal form has been used as the starting material to synthesize various gabosines and anhydrogabosines through a divergent strategy. The syntheses of anhydrogabosines involve three main transformations: α-methylation, epoxidation, and sulfur removal, whereas the syntheses of gabosines require an additional epoxide hydrolysis step. Copyright

Enantioselective synthesis of natural polyoxygenated cyclohexanes and cyclohexenes from [(p-tolylsulfinyl)methyl]-p-quinols

Exploitation of the β-hydroxysulfoxide fragment present in a number of enantiomerically pure (SR)and (SS)-[(p-tolylsulfinyl)methyl]-pquinols allowed chemo- and stereocontrolled conjugate additions of different organoaluminium reagents to the cyclohexadien

Enantioselective synthesis of (+)- and (-)-dihydroepiepoformin and (+)-epiepoformin

(Chemical Equation Presented) The enantioselective synthesis of both enantiomers of dihydroepiepoformin (1) and (+)-epiepoformin (2) was achieved from (p-tolylsulfinyl)-methyl-p-quinols (SR)- or (SS)-3 and (4R,SR)-4, respectively. Key features include the

Total synthesis of (+)-epiepoformin, (+)-epiepoxydon and (+)-bromoxone employing a useful chiral building block, ethyl (1R,2S)-5,5-ethylenedioxy-2-hydroxycyclohexanecarboxylate

Enantioselective total synthesis of (+)-epiepoformin 1, (+)-epiepoxydon 2 and (+)-bromoxone 3 using a chiral building block, ethyl (1R,2S)-5,5-ethylenedioxy-2-hydroxycyclo- hexanecarboxylate 6, is described. Since the synthesis afforded intermediates 18, 2 and 25, it accomplished a formal synthesis of (-)-theobroxide 19, (-)-phyllostine 22, (+)-herveynone 27 and (-)-asperpentyn 28. The usefulness of 6 for the synthesis of natural epoxycyclohexene derivatives was demonstrated.

The First Synthesis of (-)-Asperpentyn and Efficient Syntheses of (+)-Harveynone, (+)-Epiepoformin and (-)-Theobroxide

A generally applicable strategy for the synthesis of a range of polyoxygenated cyclohexane natural products has been developed. The enantioselective syntheses of (-)-theobroxide, a polyoxygenated cyclohexane natural compound with potent growth inducing pr