138517-53-0Relevant academic research and scientific papers
Synthesis of fluorinated amphiphiles by the reaction of protected hydroxy carbaldehyde with perfluorinated organomagnesium compounds
Kvicala, Jaroslav,Mouyrin, Jean-Christophe,Paleta, Oldrich
, p. 195 - 200 (2002)
Fluorinated amphiphilic compounds with enhanced chemical stability were synthesized by the reaction of 5-(2,2,5-trimethyl-1,3-dioxane)carbaldehyde (1) with perfluoroalkylmagnesium bromides (2), followed by deprotection. The key aldehyde 1 was prepared by
A concise synthesis of (-)-lasonolide A
Trost, Barry M.,Stivala, Craig E.,Hull, Kami L.,Huang, Audris,Fandrick, Daniel R.
supporting information, p. 88 - 91 (2014/01/23)
Lasonolide A is a novel polyketide displaying potent anticancer activity across a broad range of cancer cell lines. Here, an enantioselective convergent total synthesis of the (-)-lasonolide A in 16 longest linear and 34 total steps is described. This approach significantly reduces the step count compared to other known syntheses. The synthetic strategy utilizes alkyne-bearing substrates as core building blocks and is highlighted by stitching together two similarly complex halves via a key Ru-catalyzed alkene-alkyne coupling and macrolactionization.
Versatile synthesis of amphiphilic oligo(Aliphatic-Glycerol) layer-block dendrons with different hydrophilic-lipophilic balance values
Choi, Lai-Sheung,Chow, Hak-Fun
supporting information, p. 201 - 206 (2013/02/25)
A series of amphiphilic oligo(glycerol-aliphatic) layer-blocked dendrons with different hydrophilic-lipophilic balance values (3.5-15.0) was prepared for use in controlled drug delivery and self-assembly studies. The synthetic strategies involved first a convergent growth of the inner hydrophobic sector followed by a divergent growth of the outer hydrophilic sector. Georg Thieme Verlag Stuttgart New York.
Highly efficient stereoselective catalytic C(sp3)-H insertions with donor rhodium carbenoids generated from cyclopropenes
Archambeau, Alexis,Miege, Frederic,Meyer, Christophe,Cossy, Janine
supporting information, p. 11540 - 11544 (2013/01/15)
Rings of five and six: Donor alkenyl rhodium carbenoids generated from 3,3-dimethylcyclopropenylcarbinols exhibit high reactivity in intramolecular C-H insertions. The reactions proceed under remarkably mild conditions, tolerate the presence of the free hydroxy group, and afford an efficient and stereoselective access to a variety of functionalized carbocycles and oxygen heterocycles. Copyright
Stereoselective total synthesis of the natural (+)-lasonolide A
Kang, Sung Ho,Kang, Suk Youn,Choi, Hyeong-Wook,Kim, Chul Min,Jun, Hyuk-Sang,Youn, Joo-Hack
, p. 1102 - 1114 (2007/10/03)
The natural (+)-lasonolide A (1), an anti-tumor agent, has been synthesized via thermodynamic benzylidene formation at the C22 quaternary chiral center, use of a disulfone equivalent for elongation of the C 15-C17 three-carbon chain as well as introduction of the two trans olefins at C15 and C17, iodocyclization for the upper THP, Michael addition for the bottom THP, and intramolecular Horner-Emmons olefination for the 20-membered macrolactone.
Total Synthesis of Natural (+)-Lasonolide A
Kang, Sung Ho,Kang, Suk Youn,Kim, Chul Min,Choi, Hyeong-Wook,Jun, Hyuk-Sang,Lee, Byeong Moon,Park, Chul Min,Jeong, Joon Won
, p. 4779 - 4782 (2007/10/03)
The diastereoselective differentiation of two methylene groups of a cyclic acetal is a unique feature of a highly enantioselective total synthesis of natural (+)-Iasonolide A (see picture), which is used to create the C22 quaternary asymmetric center. Other key strategies are the use of a sulfone-sulfide as a three-carbon fragment with two latent trans double bonds and macrocyclization through an intramolecular Horner-Emmons reaction.
