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

• 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 
• 186395-72-2 (1R,3aS,4S,5R,6aR,7S,9aS,10R,10aS)-7-Isopropyl-5-methoxymethoxy-1,4,9a-trimethyl-tetradecahydro-dicyclopenta[a,d]cycloocten-10-ol 
• 194794-91-7 ((1R,3aR,6S,6aS,7S,9aR,10aS)-7-Isopropyl-6-methoxymethoxy-1,9a-dimethyl-tetradecahydro-dicyclopenta[a,d]cycloocten-4-yl)-methanol 
• 186395-85-7 (3S,3aS,4S,6aR,9R,9aS,10aR)-6-Hydroxymethyl-3-isopropyl-9,10a-dimethyl-tetradecahydro-dicyclopenta[a,d]cycloocten-4-ol 
• 186422-89-9 (S)-2-((1R,2S,3R)-2-Formyl-3-methyl-cyclopentyl)-propionic acid methyl ester 
• 120264-20-2 (R)-(+)-1-bromo-3-(1-methylethyl)cyclopentene 
• 158137-45-2 15-cyanoepoxydictymene 
• 189358-76-7 1(S)-<4-ethoxy-4-(2-methyl-3-buten-2-oxy)butyn-1-yl>-2(R)-<3-(trimethylsilyl)isopropenyl>-5(R)-methylcyclopentane 
• 158137-42-9 (3R,3aR,5aS,6R,8aR,10aS)-2,2,6-Trimethyl-9-methylene-4-oxo-dodecahydro-1-oxa-dicyclopenta[a,e]cyclooctene-3-carbaldehyde 
• 158249-59-3 1(S)-(hydroxymethyl)-2(R)-<3-(trimethylsilyl)isopropenyl>-5(R)-methylcyclopentane 
• 158249-58-2 ((1S,2R,5R)-2-Isopropenyl-5-methyl-cyclopentyl)-methanol 
• 186395-88-0 Acetic acid (1R,3aR,4S,6S,6aS,7S,9aR,10aS)-6-hydroxy-7-isopropyl-1,9a-dimethyl-tetradecahydro-dicyclopenta[a,d]cycloocten-4-ylmethyl ester 
• 186395-83-5 C₂₂H₃₈O₃ 
• 186395-84-6 (1R,3aR,6S,6aS,7S,9aR,10aS)-7-Isopropyl-6-methoxymethoxy-1,4,9a-trimethyl-tetradecahydro-dicyclopenta[a,d]cycloocten-4-ol 

Downstream Products

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

Relevant articles and documents

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.

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