17748-68-4Relevant articles and documents
Selective synthesis of 14 dehydroestranes
Rasmusson,Arth
, p. 107 - 111 (1973)
The report of the preparation and high androgenic activity of Δ14 19 nortestosterone and its 7α methyl derivative prompted the authors to disclose an alternate synthesis of these compounds. The introduction of the double bond into the 14 position of estranes has been accomplished by acid or base equilibration of an initially formed Δ15 isomer.
Synthesis of Cyclic Enones by Allyl-Palladium-Catalyzed α,β-Dehydrogenation
Huang, David,Zhao, Yizhou,Newhouse, Timothy R.
, p. 684 - 687 (2018)
The use of allyl-palladium catalysis for the one-step α,β-dehydrogenation of ketones via their zinc enolates is reported. The optimized protocol utilizes commercially available Zn(TMP)2 as base and diethyl allyl phosphate as oxidant. Notably, this transformation operates under salt-free conditions and tolerates a diverse scope of cycloalkanones.
Allyl-Palladium-Catalyzed Ketone Dehydrogenation Enables Telescoping with Enone α,β-Vicinal Difunctionalization
Chen, Yifeng,Huang, David,Zhao, Yizhou,Newhouse, Timothy R.
supporting information, p. 8258 - 8262 (2017/06/30)
The telescoping of allyl-palladium catalyzed ketone dehydrogenation with organocuprate conjugate addition chemistry allows for the introduction of aryl, heteroaryl, vinyl, acyl, methyl, and other functionalized alkyl groups chemoselectively to a wide variety of unactivated ketone compounds via their enone counterparts. The compatibility of the dehydrogenation conditions additionally allows for efficient trapping of the intermediate enolate with various electrophiles. The utility of this approach is demonstrated by comparison to several previously reported multistep sequences.
Indole diterpene synthetic studies: Development of a second-generation synthetic strategy for (+)-nodulisporic acids A and B
Smith III, Amos B.,Kuerti, Laszlo,Davulcu, Akin H.,Young, Shin Cho,Ohmoto, Kazuyuki
, p. 4611 - 4620 (2008/02/07)
(Chemical Equation Presented) A second-generation strategy for construction of (+)-nodulisporic acids A and B based on the development of a new, effective modular indole synthesis exploiting a sequential Stille cross-coupling/Buchwald- Hartwig union/cyclization tactic is disclosed. This strategy evolved due to the considerable acid instability of the C(24) hydroxyl group observed in several advanced intermediates during our first-generation approach.
