33404-85-2

Basic information

• Product Name: coriolin
• Synonyms: coriolin;(1aS,3S,7aR)-3bβ,4,5,6,6aβ,7-Hexahydro-4β,7α-dihydroxy-3aα,5,5-trimethylspiro[cyclopenta[4,5]pentaleno[1,6a-b]oxirene-3(3aH),2'-oxiran]-2(1aH)-one;(3S,7aR)-3aα,5,5-Trimethyl-4β,7α-dihydroxy-1aβ,2,3bβ,4,5,6,6aβ,7-octahydrospiro[cyclopenta[4,5]pentaleno[1,6a-b]oxirene-3(3aH),2'-oxirane]-2-one
• CAS NO: 33404-85-2
• Molecular Formula: C15H20O5
• Molecular Weight: 280.318
• Mol File: 33404-85-2.mol

Chemical Properties

• Boiling Point: 479°Cat760mmHg
• Flash Point: 183.2°C
• Appearance: /
• Density: 1.46g/cm³
• CAS DataBase Reference: coriolin(CAS DataBase Reference)
• NIST Chemistry Reference: coriolin(33404-85-2)
• EPA Substance Registry System: coriolin(33404-85-2)

Safety Data

• Hazardous Substances Data: 33404-85-2(Hazardous Substances Data)

Upstream product

• 74181-88-7 (3aS,3bR,4R,6aS,7S)-3-Benzenesulfinyl-4,7-dihydroxy-3,3a,5,5-tetramethyl-3,3a,3b,4,5,6,6a,7-octahydro-cyclopenta[a]pentalen-2-one 
• 74145-68-9 (3aβ,3bα,4α,6aα,7β)-3a,3b,5,6,6a,7-hexahydro-3a,5,5-trimethyl-4,7-dihydroxy-3-methylene-4H-cyclopenta<4,5>pentalen-2-one 
• 74181-87-6 (3ε,3aβ,3bα,4α,6aα,7β)-3a,3b,5,6,6a,7-hexahydro-3,3a,5,5-tetramethyl-4,7-dihydroxy-3-(phenylthio)-4H-cyclopenta<4,5>pentalen-2-one 
• 74145-66-7 C₁₅H₂₄O₃ 
• 74145-65-6 (3aS,3bR,4R,6aR)-3,3a,5,5-Tetramethyl-2,3,3a,3b,4,5,6,6a-octahydro-1H-cyclopenta[a]pentalene-2,4-diol 
• 72008-79-8 (1RS,2RS,6SR,7SR,8RS,11RS)-7,8-epoxy-11-methoxymethoxy-1,4,4-trimethyltricyclo<6.3.0.0^2,6>undecan-3-one ethylene acetal 
• 72008-73-2 (1RS,2RS,6SR,7SR,8RS,11RS)-7,8,11-trihydroxy-1,4,4-trimethyltricyclo<6.3.0.0^2,6>undecan-3-one 
• 73828-07-6 (1SR,2RS,6RS,11RS)-11-hydroxy-1,4,4-trimethyltricyclo<6.3.0.0^2,6>undec-7-en-3-one 
• 73828-14-5 (3aSR,3bRS,4RS,6aSR,7SR)-4,7-diacetoxy-3,3a,3b,4,5,6,6a,7-octahydro-3a,5,5-trimethyl-3-methylene-2H-cyclopentapentalen-2-one 
• 3883-57-6 3-acetoxy-2-methylcyclopent-2-en-1-one 
• 72008-65-2 4-acetoxy-6,6-dimethylcyclohex-2-enone ethylene acetal 
• 74145-61-2 (3aR,6S,6aR)-2,2,6-Trimethyl-6-(1-methyl-2-oxo-propyl)-hexahydro-pentalene-1,5-dione 
• 74145-62-3 (3aβ,3bα,6aα)-3a,3b,5,6,6a,7-hexahydro-3,3a,5,5-tetramethylcyclopenta<4,5>pentalene-2,4-dione 
• 74145-63-4 (3aβ,3bα,6aα)-3,3a,3b,5,6,6a-hexahydro-3,3a,5,5-tetramethylcyclopenta<4,5>pentalene-2,4-dione 

Relevant articles and documents

Total synthesis of (-)-coriolin

An efficient synthetic method for (-)-coriolin has been developed on the basis of a [3+2] cycloaddition reaction of a 1-(methylthio)-2-siloxyallyl cationic species and vinylsulfides. An enantiomerically pure C-ring unit was prepared through optical resolution of five-membered allyl ester 6b using a lipase. The first [3+2] cycloaddition reaction of C-ring unit (S)-7 gave bicyclic ketones 8 and 9, which were easily converted into vinyl sulfide 11. Stereoselective construction of the A-ring was achieved by the second [3+2] cycloaddition reaction of the BC-ring unit. New methods for introduction of the oxygen functional groups to the triquinane skeleton were also developed for the last stages of the total synthesis. Thus, the C7 hydroxyl group was introduced by epoxidation of dienol silyl ether 17, and stereocontrolled construction of the spiro epoxide moiety was accomplished on the basis of a Darzens-type reaction.

Radical-Type Cyclization of Diens, VI. - Total Synthesis of (-)-Coriolin and (-)-Epicoriolin from (S)-(+)-Carvone

(3aR,4S,6aS)-(+)-4-(4-Methoxybenzyloxy)-6a-methyl-3,3a,4,6a-tetrahydro-2H-cyclopentafuran-2-one (10) and (3aR,3bR,4R,6aS,7S,7aS)-(-)-decahydro-4,7-dihydroxy-3a,5,5-trimethyl-3-methylene-2H-cyclopentapentalen-2-one (21) are the key intermediates in t

Stereospecific Total Synthesis of dl-Coriolin and dl-Coriolin B

The total synthesis of the title compounds are described.The starting materials were the enedione 6 and the siloxy diene 27.Cycloaddition of these compounds afforded 28, which was converted to 30.Degradation of enone 30 gave methyl ketone 32, which upon c

THE TOTAL SYNTHESIS OF (+/-)-CORIOLIN

The first total synthesis of (+/-)-coriolin from the tricyclo 6-4-5-fused ring photo-adduct through the key tricyclo 5-5-5-fused ring intermediate, 7,8,11-trihydroxy-1,4,4-trimethyltricyclo2,6>undecan-3-one, is described.

The total synthesis of (±)-coriolin

The first total synthesis of (±)-coriolin from the tricyclo 6-4-5-fused ring photo-adduct through the key tricyclo 5-5-5-fused ring intermediate, 7,8,11 - trihydroxy - 1,4,4 - trimethyltricyclo[6.3.0.02,6]undecan - 3 - one, is described.

THE total synthesis of (±)-coriolin

The first total synthesis of (±)-coriolin from the tricyclo 6-4-5-fused ring photo-adduct through the key tricyclo 5-5-5-fused ring intermediate, 7,8,11 - trihydroxy - 1,4,4 - trimethyltricyclo[6.3.0.02,6]undecan - 3 - one, is described.