89002-20-0

Basic information

• Product Name: (+)-Epoxydictymene
• Synonyms: (+)-Epoxydictymene;(2aR,2aα,4aα,6aβ,9aβ,10bβ)-1,2a,3,4a,5,6,6a,7,8,9,9a,10,10a,10b-Tetradecahydro-3,3,9β,10aα-tetramethyl-6-methylene-2H-4-oxacyclopenta[5,6]cycloocta[1,2,3-cd]pentalene;Epoxydictymene
• CAS NO: 89002-20-0
• Molecular Formula: C20H32O
• Molecular Weight: 288.47
• Mol File: 89002-20-0.mol

Chemical Properties

• Boiling Point: 359.6°C at 760 mmHg
• Flash Point: 167°C
• Appearance: /
• Density: 1g/cm³
• Vapor Pressure: 4.86E-05mmHg at 25°C
• Refractive Index: 1.52
• CAS DataBase Reference: (+)-Epoxydictymene(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-Epoxydictymene(89002-20-0)
• EPA Substance Registry System: (+)-Epoxydictymene(89002-20-0)

Safety Data

• Hazardous Substances Data: 89002-20-0(Hazardous Substances Data)

Usage

InChI:InChI=1/C20H32O/c1-12-6-7-14-13(2)10-17-18-16(19(3,4)21-17)8-9-20(18,5)11-15(12)14/h12,14-18H,2,6-11H2,1,3-5H3/t12-,14+,15+,16-,17+,18?,20-/m1/s1

Upstream product

• 194794-90-6 (1R,3aR,4R,6S,6aS,7S,9aR,10aS)-7-Isopropyl-6-methoxymethoxy-1,4,9a-trimethyl-tetradecahydro-dicyclopenta[a,d]cycloocten-4-ol 
• 194794-76-8 (1R,3aS,4S,5R,6aR,7S,9aS,10R,10aS)-7-Isopropyl-5-methoxymethoxy-1,4-dimethyl-tetradecahydro-dicyclopenta[a,d]cycloocten-10-ol 
• 194794-78-0 (1R,3aR,4S,6aR,7S,9aR,10aS)-7-Isopropyl-5-methoxymethoxy-1,4,9a-trimethyl-tetradecahydro-dicyclopenta[a,d]cyclooctene 
• 186395-90-4 (2aR,4aS,6S,6aR,9R,9aS,10aR,10bS)-tetradecahydro-3,3,9,10a-tetramethyl-2H-4-oxacyclopenta[5,6]cycloocta(1,2,3-cd)pentalene-6-methanol acetate 
• 186395-79-9 Acetic acid (1R,3aR,4R,6S,6aS,7S,9aR,10aS)-6-hydroxy-7-isopropyl-1,9a-dimethyl-tetradecahydro-dicyclopenta[a,d]cycloocten-4-ylmethyl ester 
• 186395-69-7 (1R,4S,4aR,7R,7aS)-1-((S)-3-Isopropyl-cyclopent-1-enyl)-4,7-dimethyl-hexahydro-cyclopenta[c]pyran-3-one 
• 186395-75-5 (1R,3aR,4S,6aS,7S,9aR,10aS)-7-Isopropyl-1,4,9a-trimethyl-dodecahydro-dicyclopenta[a,d]cycloocten-5-one 
• 186395-73-3 (1R,3aR,4S,6aR,7S,9aR,10aS)-7-Isopropyl-1,4,9a-trimethyl-dodecahydro-dicyclopenta[a,d]cycloocten-5-one 
• 194794-77-9 Selenocarbonic acid O-((1R,3aS,4S,5R,6aR,7S,9aS,10R,10aS)-7-isopropyl-5-methoxymethoxy-1,4,9a-trimethyl-tetradecahydro-dicyclopenta[a,d]cycloocten-10-yl) ester Se-phenyl ester 
• 194794-87-1 (1R,3aR,4S,6R,6aS,7S,9aR,10aS)-7-Isopropyl-6-methoxymethoxy-1,4,9a-trimethyl-dodecahydro-dicyclopenta[a,d]cycloocten-5-one 
• 186395-86-8 (1R,3aS,4S,5R,6aR,7S,9aS,10aS)-7-Isopropyl-5-methoxymethoxy-1,4,9a-trimethyl-dodecahydro-dicyclopenta[a,d]cycloocten-10-one 
• 186395-71-1 (1R,3aS,4S,5R,6aR,7S,9aS,10aS)-7-Isopropyl-5-methoxymethoxy-1,4-dimethyl-dodecahydro-dicyclopenta[a,d]cycloocten-10-one 
• 186395-78-8 (1R,3aR,6S,6aS,7S,9aR,10aS)-7-Isopropyl-6-methoxymethoxy-1,9a-dimethyl-4-methylene-tetradecahydro-dicyclopenta[a,d]cyclooctene 
• 186395-76-6 (1R,3aR,4S,6R,6aS,7S,9aR,10aS)-6-Hydroxy-7-isopropyl-1,4,9a-trimethyl-dodecahydro-dicyclopenta[a,d]cycloocten-5-one 

Downstream Products

• 89002-24-4 C₂₇H₃₈BrNO₄ 
• 89002-24-4 C₂₇H₃₈BrNO₄ 

Relevant articles and documents

Tandem use of cobalt-mediated reactions to synthesize (+)- epoxydictymene, a diterpene containing a trans-fused 5-5 ring system

The diterpene (+)-epoxydictymene has been synthesized in 20 steps using the asymmetry of (R)-pulegone and several substrate-controlled diastereoselective reactions to prepare the natural product in its natural configuration. Three of the four rings were assembled with two consecutive intramolecular reactions involving dicobalt hexacarbonyl complexes of alkynes: a Lewis acid-promoted Nicholas reaction and a Pauson-Khand reaction. The construction of the strained trans-3-oxabicyclo[3.3.0]octane ring system of the natural product presented a significant challenge. To this end, several radical and anionic cyclizations were studied, the latter leading to (+)-epoxydictymene.

Total synthesis of (+)-epoxydictymene. Application of alkoxy-directed cyclization to diterpenoid construction

An enantioselective synthesis of (+)-epoxydictymene (1) is reported. Condensation of the enantiopure aldehydo ester 5 with (S)-3-isopropylcyclopentenyllithium proceeds selectively to afford 13. Once this lactone was methylenated with the Tebbe reagent, th

Highly enantioselective total synthesis of natural epoxydictymene. An alkoxy-directed cyclization route to highly strained trans-oxabicyclo[3.3.0]octanes

An enantioselective synthesis of (+)-epoxydictymene, which involves efficient construction of the strained oxabicyclo[3.3.0]octane subunit by irradiation with iodosobenzene diacetate and iodine in cyclohexane solution, is reported.