130796-32-6Relevant articles and documents
Asymmetric Total Syntheses of Aetheramides and Their Stereoisomers: Stereochemical Assignment of Aetheramides
Qi, Na,Allu, Srinivasa Rao,Wang, Zhanlong,Liu, Qiang,Guo, Jian,He, Yun
supporting information, p. 4718 - 4721 (2016/09/28)
The concise total syntheses of the potent HIV inhibitors aetheramides A and B (IC50 values of 15 and 18 nM), as well as three pairs of their stereoisomers, were achieved, which allowed the complete stereochemical assignment of aetheramides for the first time. With a longest linear sequence of 15 steps, the convergent, fully stereocontrolled route provided aetheramides A and B in 5.3% and 3.6% yields, respectively. The synthetic strategy features efficient Stille coupling for macrocyclization, asymmetric aldol reactions to establish the ambiguous stereochemistries at C-17 and C-26, and implementation of mild conditions to avoid the epimerization of the sensitive polyketide moiety and the migration of the labile lactone.
Oxidative cyclization of γ-alkylidene butenolides. Stereoselective preparation of spirolactones
Galan-Fernandez, Raquel,Clemente-Tejeda, David,Bermejo, Francisco A.
, p. 1 - 14 (2013/01/16)
A new route to 1,6-dioxaspiro[4.4]non-3-en-2-ones is established by bromoetherification of dihydroxybutenolides. An asymmetric total synthesis of 8-epi-crassalactone D starting from methyl cinnamate has been accomplished. ARKAT-USA, Inc.
Stereocontrolled synthesis of gem-difluoromethylenated goniodiols and goniothalamin epoxides based on ring-closing metathesis
You, Zheng-Wei,Zhang, Xingang,Qing, Feng-Ling
, p. 2535 - 2542 (2008/02/04)
An efficient and general method to stereoselectively synthesize gem-difluoromethylenated goniodiols and goniothalamin epoxides has been developed. The introduction of a gem-difluoromethyl-containing group was achieved by the reaction of aldehydes with 3-bromo-3,3-difluoropropene in the presence of indium. The gem-difluoromethylenated α,β-unsaturated- δ-lactone moiety was constructed through the ring-closing metathesis of highly electron-deficient gew-difluoromethylenated acryloyl esters by Grubbs' II catalyst in toluene at reflux. Georg Thieme Verlag Stuttgart.