89002-20-0Relevant articles and documents
Tandem use of cobalt-mediated reactions to synthesize (+)- epoxydictymene, a diterpene containing a trans-fused 5-5 ring system
Jamison, Timothy F.,Shambayati, Soroosh,Crowe, William E.,Schreiber, Stuart L.
, p. 4353 - 4363 (2007/10/03)
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
Paquette, Leo A.,Sun, Li-Qiang,Friedrich, Dirk,Savage, Paul B.
, p. 8438 - 8450 (2007/10/03)
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
Paquette, Leo A.,Sun, Li-Qiang,Friedrich, Dirk,Savage, Paul B.
, p. 195 - 198 (2007/10/03)
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.