1379822-84-0Relevant academic research and scientific papers
Enantioselective Total Synthesis of Diocollettines A
Kawamoto, Yuichiro,Kobayashi, Toyoharu,Ito, Hisanaka
, p. 5813 - 5816 (2019)
The first enantioselective total synthesis of diocollettines A was accomplished in only six steps from a known compound. A short and practical synthetic route was disclosed, featuring an intensive investigation of the stereoselective aldol reaction as a key step using an easily prepared aldehyde moiety and an enone derivative. The synthetic scheme also includes the efficient stereocontrolled construction of the tricyclic skeleton of diocollettines A by intramolecular acetal formation, stereoselective dihydroxylation, and intramolecular ether cyclization.
Synthesis of prostaglandin analogues, latanoprost and bimatoprost, using organocatalysis via a key bicyclic enal intermediate
Pr??vost, S??bastien,Thai, Karen,Sch??tzenmeister, Nina,Coulthard, Graeme,Erb, William,Aggarwal, Varinder K.
, p. 504 - 507 (2015/03/05)
Two antiglaucoma drugs, bimatoprost and latanoprost, which are analogues of the prostaglandin, PGF2?±, have been synthesized in just 7 and 8 steps, respectively. The syntheses employ an organocatalytic aldol reaction that converts succinaldehyde into a key bicyclic enal intermediate, which is primed for attachment of the required lower and upper side chains. By utilizing the crystalline lactone, the drug molecules were prepared in >99% ee.
Total synthesis of (-)-blepharocalyxin D and analogues
Cons, Benjamin D.,Bunt, Adam J.,Bailey, Christopher D.,Willis, Christine L.
supporting information, p. 2046 - 2049 (2013/06/05)
An efficient strategy for the total synthesis of (-)-blepharocalyxin D and an analogue is described. The key step involves an acid-mediated cascade process in which reaction of methyl 3,3-dimethoxypropanoate with γ,δ- unsaturated alcohols possessing diastereotopic styrenyl groups gives trans-fused bicyclic lactones with the creation of two rings and four stereocenters in one pot.
A chemoenzymatic asymmetric synthesis of (+)-strictifolione
Ghadigaonkar, Sneha,Koli, Mrunesh R.,Gamre, Sunita S.,Choudhary, Manoj K.,Chattopadhyay, Subrata,Sharma, Anubha
, p. 1093 - 1099 (2012/11/06)
A chemoenzymatic asymmetric synthesis of the title compound has been developed using an efficient lipase-catalyzed acylation and a chiral reagent-directed diastereoselective allylation as the key steps for incorporating the stereogenic centers. A cross me
Bicyclic oxygen heterocycles from γ,δ-unsaturated alcohols: Synthetic targets inspired by blepharocalyxin D
Bunt, Adam J.,Bailey, Christopher D.,Cons, Benjamin D.,Edwards, Sophie J.,Elsworth, Jon D.,Pheko, Tshepo,Willis, Christine L.
supporting information; experimental part, p. 3901 - 3904 (2012/06/04)
trans-2,8-Dioxabicyclodecanes were prepared in high yield with the creation of up to three stereocenters in a single pot by the acid-mediated reaction of γ,δ-unsaturated alcohols with aldehydes (see scheme, Bn=benzyl). This versatile reaction enables the stereoselective introduction of substituents at the C3, C4, C7, and C9 positions of the bicyclic framework. Copyright
