1133797-34-8Relevant academic research and scientific papers
Total synthesis of incarviditone and incarvilleatone
Brown, Patrick D.,Willis, Anthony C.,Sherburn, Michael S.,Lawrence, Andrew L.
, p. 4537 - 4539 (2012)
The total synthesis of the racemic natural products (±)- incarviditone and (±)-incarvilleatone has been accomplished in three steps via biomimetic dimerization of (±)-rengyolone. Homochiral dimerization of (±)-rengyolone affords (±)-incarviditone through a domino oxa-Michael/Michael sequence. Heterochiral dimerization, involving a domino oxa-Michael/Michael/aldol reaction sequence, affords (±)- incarvilleatone. Single-crystal X-ray analysis of a derivative of (±)-incarviditone has resulted in revision of the originally proposed structure.
Bio-inspired Domino oxa-Michael/Diels–Alder/oxa-Michael Dimerization of para-Quinols
Green, Nicholas J.,Connolly, Catherine A.,Rietdijk, Koen P. W.,Nichol, Gary S.,Duarte, Fernanda,Lawrence, Andrew L.
, p. 6198 - 6202 (2018)
A bio-inspired, pyrrolidine-mediated, dimerization of para-quinols has been developed. It represents one of the most complex, yet general, dimerization reactions ever disclosed, selectively forming four new bonds, four new rings, and eight new contiguous stereogenic centres. The para-quinol starting materials are easily handled, bench-stable compounds, accessed in just one step from aromatic feedstocks. The reaction can be scaled up to give grams of polycyclic material, primed for further elaboration.
Phosphazene-catalyzed desymmetrization of cyclohexadienones by dithiane addition
Horwitz, Matthew A.,Massolo, Elisabetta,Johnson, Jeffrey S.
, p. 762 - 767 (2017)
We report a desymmetrization of cyclohexadienones by intramolecular conjugate addition of a tethered dithiane nucleophile. Mild reaction conditions allow the formation of diversely functionalized fused bicyclic lactones. The products participate in facially selective additions from the convex surface, leading to allylic alcohol derivatives.
Total synthesis of incarvilleatone and incarviditone: Insight into their biosynthetic pathways and structure determination
Zhao, Kun,Cheng, Gui-Juan,Yang, Hongzhi,Shang, Hai,Zhang, Xinhao,Wu, Yun-Dong,Tang, Yefeng
, p. 4878 - 4881 (2012)
A concise biomimetic total synthesis of incarvilleatone and incarviditone is achieved in one pot via the highly stereoselective hetero-and homodimerization of (±)-rengyolone, respectively. The structure of incarviditone is revised on the basis of spectroscopic and computational evidence.
Total synthesis of incargranine A
Brown, Patrick D.,Lawrence, Andrew L.
supporting information, p. 1698 - 1702 (2019/02/20)
Synthetic studies into the origins of the alkaloid incargranine A have resulted in the development of a four-step (longest linear sequence) total synthesis. This synthesis has been scaled-up to provide gram-scale quantities of material, which would alternatively require extraction of several metric-tons of dried-whole Chinese Trumpet-Creeper plants (Incarvillea mairei var. grandiflora).
Catalytic enantioselective silylation of acyclic and cyclic triols: Application to total syntheses of cleroindicins D, F, and C
You, Zhen,Hoveyda, Amir H.,Snapper, Marc L.
supporting information; experimental part, p. 547 - 550 (2009/04/14)
(Chemical Equation Presented) Pick one out of three: Acyclic and cyclic 1,2,3-triols are silylated with exceptional site- and enantioselectivity by a small-molecule catalyst to afford silyl ethers having a neighboring diol moiety. The new process is appli
