90129-47-8Relevant articles and documents
Total synthesis of crotophorbolone
Chen, Ting,Fu, Shaomin,Liu, Bo,Sun, Ying,Tu, Canhui,Yu, Tianzi
, p. 7177 - 7181 (2020)
As a natural diterpenoid, crotophorbolone possesses a challenging trans,trans-5/7/6 framework decorated with six contiguous stereogenic centers and is structurally and biogenetically related to tigliane-type diterpenoids with intriguing bioactivities such as phorbol and prostratin. Based on the convergent strategy, we completed an eighteen-step total synthesis of crotophorbolone starting from (-)-carvone and (+)-dimethyl-2,3-O-isopropylidene-l-tartrate. The key elements of the synthesis involve expedient installation of the six-membered ring and the five-membered ring with multiple functional groups at an early stage, cyclization of the seven-membered ring through alkenylation of the ketone between the five-membered ring and the six-membered ring, functional group-sensitive ring-closing metathesis and final selective introduction of hydroxyls at C20 and C4. This journal is
DoE (Design of Experiments) assisted allylic hydroxylation of enones catalysed by a copper-aluminium mixed oxide
Garcia-Cabeza, Ana Leticia,Marin-Barrios, Ruben,Azarken, Redouan,Moreno-Dorado, F. Javier,Ortega, Maria J.,Vidal, Hilario,Gatica, Jose M.,Massanet, Guillermo M.,Guerra, Francisco M.
, p. 8307 - 8314 (2014/01/06)
The allylic hydroxylation of enones using dioxygen as the oxidant has been studied. The reaction was first examined in the absence of any catalyst, using β-ionone as a model substrate. Then a new copper-aluminium mixed oxide, Cu-Al Ox, was prepared and ch
Total synthesis and structure-activity relationship study of the potent cAMP signaling agonist (-)-alotaketal A
Huang, Jinhua,Yang, Jessica R.,Zhang, Jin,Yang, Jiong
, p. 3212 - 3222 (2013/06/05)
A detailed account of the first total synthesis of alotaketal A, a tricyclic spiroketal sesterterpenoid that potently activates the cAMP signaling pathway, is provided. The synthesis employs both intra- and intermolecular reductive allylation of esters for assembling one of the fragments and their coupling. A Hg(OAc)2-mediated allylic mercuration is used to introduce the C22-hydroxyl group. The subtle influence of substituents over the course of the spiroketalization process is revealed. The synthesis confirms the relative and absolute stereochemistry of (-)-alotaketal A and allows verification of alotaketal A's effect over cAMP signaling using reporter-based FRET imaging assays with HEK 293T cells. Our studies also revealed alotaketal A's unique activity in selectively targeting nuclear PKA signaling in living cells. The Royal Society of Chemistry 2013.
γ-oxygenation of α,β-unsaturated esters by vinylogous O-nitroso mukaiyama aldol reaction
Tian, Guo-Qiang,Yang, Jiong,Rosa-Perez, Kellymar
scheme or table, p. 5072 - 5074 (2010/12/25)
A practical procedure has been developed for γ-oxygenation of α,β-unsaturated esters by a vinylogous O-nitroso Mukaiyama aldol reaction followed by a one-pot N-O bond heterolysis of the in situ generated γ-aminoxy-α,β-unsaturated esters.
Highly Efficient Conversion of (-)-Carvone to (+)-5β-Hydroxycarvone
Miyashita, Masaaki,Suzuki, Toshio,Yoshikoshi, Akira
, p. 3377 - 3380 (2007/10/02)
(-)-Carvone has been efficiently transformed into (+)-5β-hydroxycarvone (1), which is expected to play an important role as a potential precursor or as a chiral template in the synthesis of natural products.Both hydroxy selenides 4 and 5, obtained by the
