80677-96-9

Basic information

• Product Name: (3aR,3bβ,6aβ)-4β-Hydroxy-3aα,5,5-trimethyl-3-methylene-1α,7aα-epoxydecahydro-2H-cyclopenta[a]pentalene-2-one
• Synonyms: (1aS,3bβ,6aβ,7aS)-3,3a,3b,4,5,6,6a,7-Octahydro-4β-hydroxy-3aα,5,5-trimethyl-3-methylenecyclopenta[4,5]pentaleno[1,6a-b]oxiren-2(1aβH)-one;(3aR,3bβ,6aβ)-4β-Hydroxy-3aα,5,5-trimethyl-3-methylene-1α,7aα-epoxydecahydro-2H-cyclopenta[a]pentalene-2-one;Hypnophilin
• CAS NO: 80677-96-9
• Molecular Formula: C15H20O3
• Molecular Weight: 248.3175
• Mol File: 80677-96-9.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (3aR,3bβ,6aβ)-4β-Hydroxy-3aα,5,5-trimethyl-3-methylene-1α,7aα-epoxydecahydro-2H-cyclopenta[a]pentalene-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: (3aR,3bβ,6aβ)-4β-Hydroxy-3aα,5,5-trimethyl-3-methylene-1α,7aα-epoxydecahydro-2H-cyclopenta[a]pentalene-2-one(80677-96-9)
• EPA Substance Registry System: (3aR,3bβ,6aβ)-4β-Hydroxy-3aα,5,5-trimethyl-3-methylene-1α,7aα-epoxydecahydro-2H-cyclopenta[a]pentalene-2-one(80677-96-9)

Safety Data

• Hazardous Substances Data: 80677-96-9(Hazardous Substances Data)

Upstream product

• 17197-84-1 5,5-dimethylcyclopent-2-enone 
• 74552-31-1 (6R,7R)-(-)-7-Hydroxy-3-oxabicyclo<4.3.0>non-1-en-9-on 
• 127060-84-8 (1S,3aR,6R,6aR)-(-)-6-Benzoyloxy-3,3a,4,5,6,6a-hexahydro-1,5,5-trimethyl-1-(2-oxopropyl)-2(1H)-pentalenon 
• 127060-83-7 (1S,3aR,6R,6aR)-(+)-6-(Benzoyloxy)-1-(2-chlor-2-propenyl)-3,3a,4,5,6,6a-hexahydro-1,5,5-trimethyl-2(1H)-pentalenon 
• 127001-14-3 (3aS,3bR,4R,6aS)-(-)-6-(Benzoyloxy)-3,3a,3b,4,5,6,6a,7-octahydro-3a,5,5-trimethyl-2H-cyclopentapentalen-2-on 
• 119433-11-3 (1R,2R,3R,5R,8R)-(+)-8-Benzoyloxy-2,7,7-trimethylbicyclo<3.3.0>octan-3-ol 
• 127060-82-6 (1R,3aR,6R,6aR)-(+)-6-(Benzoyloxy)-3,3a,4,5,6,6a-hexahydro-1,5,5-trimethyl-2(1H)-pentalenon 
• 127000-11-7 (3RS,3aR,3bR,4R,6aS)-3,3a,3b,4,5,6,6a,7-Octahydro-4-hydroxy-3-(hydroxymethyl)-3a,5,5-trimethyl-2H-cyclopentapentalen-2-on 
• 102628-62-6 (3aR,3bS,4S,6aS)-(-)-3,3a,3b,4,5,6,6a,7-octahydro-4-hydroxy-3a,5,5-trimethylcyclopenta<4.5>pentalen-2-one 
• 127000-12-8 (+)-Praehypnophilin 
• 110528-25-1 (3α,3aα,3bβ,6aβ,7aα)-decahydro-3-(benzoyloxy)-2,2,3b-trimethyl-5-oxo-1H-cyclopentapentalene 
• 110528-24-0 Benzoic acid (3S,3aR,3bS,6aS,7aR)-3b-hydroxy-2,2-dimethyl-2,3,3a,3b,6,6a,7,7a-octahydro-1H-cyclopenta[a]pentalen-3-yl ester 
• 98330-93-9 (3α,3aα,6aβ,7aα)-2,3,3a,5,6,6a,7,7a-octahydro-3-(benzoyloxy)-2,2-dimethyl-5-oxo-1H-cyclopentapentalene 
• 110528-30-8 (3α,3aα,3bβ,4α,4β,7aα)-2,3,3a,3b,4,5,7,7a-octahydro-3-hydroxy-4-(hydroxymethyl)-2,2,3b-trimethyl-5-oxo-1H-cyclopentapentalene 

Relevant articles and documents

Applications of the squarate ester cascade to the expeditious synthesis of hypnophilin, coriolin, and ceratopicanol

The first applications of the squarate ester cascade to natural products synthesis have been realized. Only 10 laboratory steps mediate the conversion of diisopropyl squarate to (±)-hypnophilin (8). Key reactions include a combination of chlorination, reduction, dehydration, and oxidation maneuvers in the proper sequence. A penultimate precursor to 8 has previously been converted into coriolin (9), thereby allowing a formal synthesis of racemic 9 also to be claimed. A rather different strategy was employed to arrive at (±)-ceratopicanol (10). Of the seven steps involved, three consisted of the use of lithium in liquid ammonia. The three divergent synthetic objectives realized in these experiments involved (a) generation of an extended enolate anion and its regioselective C-methylation at the γ-carbon; (b) unprecedented reductive cleavage of a β-isopropoxy group in a 2,3-diisopropoxy-2-cyclopentenone setting; and (c) conventional conversion of an α-alkoxy ketone to the parent carbonyl system. Thus, the appreciable enhancement in structural complexity offered by the squarate cascade holds considerable potential for the concise synthesis of constitutionally intricate targets.

Three-component coupling via the squarate ester cascade as a concise route to the bioactive triquinane sesquiterpene hypnophilin.

[reaction: see text] A squarate ester cascade is used to provide in one step, via the coupling of three reactants, a highly oxygenated linear triquinane product. The latter is transformed in nine steps into hypnophilin. The access route involves a combination of chlorination, reduction, dehydration, and oxidation maneuvers in the proper sequence.

Chemistry and Stereochemistry of Iridoids, XVI. - EPC-Synthesis of (-)-Hypnophilin

The synthesis of enantiomerically pure (-)-hypnophilin (27) from (6R,7R)-(-)-7-hydroxy-3-oxabicyclonon-1-en-9-one (1) is described. 1 was obtained in 93 percent yield from catalpol, which is readily available from the aqueous sodium carbonate extra

Intramolecular 1,3-Diyl Trapping Reactions. Total Synthesis of (+/-)-Hypnophilin and (+/-)-Coriolin. Formation of the Trans-Fused Bicyclooctane Ring System

The intramolecular 1,3-diyl trapping reaction served as the key step in total synthesis of (+/-)-coriolin (1) and the first total synthesis of (+/-)-hypnophilin (3).In the process, four of the required eight (coriolin) or six (hypnophilin) stereocenters w