189164-75-8Relevant academic research and scientific papers
Formal synthesis of borrelidin: A highly enantio- and diastereoselective access to the Morken's C2-C12 intermediate
Gembus, Vincent,Karmazin, Lydia,Uguen, Daniel,Zoller, Thomas
, p. 359 - 380 (2019/02/25)
In contrast to methyl and isobutyl phenyl sulfone, condensing under basic conditions higher alkyl sulfones and trans-2,3-epoxy-butanol 13c (or its O-benzyl and O-silyl derivatives) proved unfeasible, a difficulty that was overcome by using mono ethers of trans-2,3-epoxy-butane-1,4-diol 35c as the electrophilic reagents. Thus, adding excess BuLi to a mixture of the benzyl ether 35b and sulfone ent-12a, a stereodiad sulfone prepared in pure state from the R-Roche ester, via the O-trityloxy-sulfone ent-12c (X-ray), gave, after elimination by column chromatography of the side-formed regioisomer, a diolsulfone that was next converted to sulfone 20 by means of conventional functional-group modifications. Reacting like-wise this sulfone with the parent O-PMB derivative 35a, and then proceeding to the same purification process and function adjustment, delivered the title fragment in virtually pure state.
Synthesis of the C8-C16 fragment of amphidinolide R
Reddy, Chada Raji,Ramesh, Palacherla,Rao, Nagavaram Narsimha
, p. 1532 - 1536 (2015/02/18)
An asymmetric synthesis of the C8-C16 fragment with several stereogenic centers of amphidinolide R, is described. The key reaction, Sharpless asymmetric epoxidation has provided the basis for generation of the required stereocenters. The target fragment was accomplished in a convergent manner in nine steps (longest linear synthesis of the sequence) and 32% overall yield was obtained starting from 2-butene-1,4-diol.
An efficient strategy for the synthesis of endocyclic enol ethers and its application to the synthesis of spiroacetals
Fuwa, Haruhiko,Sasaki, Makoto
supporting information; experimental part, p. 2549 - 2552 (2009/05/26)
(Chemical Equation Presented) An efficient strategy for the synthesis of endocyclic enol ethers based on a Suzuki-Miyaura coupling/ring-closing metathesis sequence has been developed. The strategy has successfully been applied to the synthesis of spiroacetals, including cytotoxic marine metabolites attenols A and B.
Studies directed toward the syntheses of amphidinolides: Formal total synthesis of (-)-amphidinolide P
Chakraborty, Tushar K.,Das, Sanjib
, p. 3387 - 3390 (2007/10/03)
A formal total synthesis of (-)-amphidinolide P (1) has been achieved via an efficient convergent strategy for the stereoselective construction of the two advanced intermediates 2 and 3, used recently by Williams et al. in their synthesis of the same mole
Anti-Markovnikov opening of trisubstituted epoxy alcohols: Application in the synthesis of 2-methyl-1,3-diols
Chakraborty, Tushar K.,Dutta, Shantanu
, p. 1257 - 1259 (2007/10/03)
2-Methyl-1,3-diols are synthesized by regioselectively opening trisubstituted epoxides, prepared from 2-methylbut-2-en-1-ols at the more substituted carbon using Cp2TiCl-cyclohexa-1,4-diene.
Synthetic studies on tautomycin synthesis of segment B
Tsuboi, Katsunori,Ichikawa, Yoshiyasu,Naganawa, Atsushi,Isobe, Minoru,Ubukata, Makoto,Isono, Kiyoshi
, p. 5083 - 5102 (2007/10/03)
The synthesis of Segment B corresponding to the C26-C17 portion of tautomycin was accomplished by coupling reaction between the epoxide (Sub-segment B-l) and the dithiane (Subsegment B-2). The degradation product of tautomycin corresponding to the C26-C19 portion was also synthesized from Sub-segment B-1.
