89104-05-2Relevant academic research and scientific papers
A Unified Synthetic Approach to Optically Pure Curvularin-Type Metabolites
Allu, Srinivasa Rao,Banne, Sreenivas,Jiang, Jia,Qi, Na,Guo, Jian,He, Yun
, p. 7227 - 7237 (2019/06/07)
A unified and concise approach to the synthesis of nine curvularin-type metabolites and two analogues has been developed with few steps and high yields. Among them, sumalactones A-D were synthesized for the first time. The key steps in this approach inclu
Total Synthesis of Tetraketide and Cryptorigidifoliol i via a Sequential Allylation Strategy
Padhi, Birakishore,Reddy, G. Sudhakar,Mohapatra, Debendra K.
, p. 2788 - 2796 (2016/12/06)
A unified and efficient synthetic route for both tetraketide (1) and cryptorigidifoliol I (2) has been devised successfully from commercially available starting materials in 11 and 17 steps, with 16% and 11% overall yields, respectively. Highlights of the syntheses involved sequential Lewis acid-catalyzed highly regio- and diastereoselective allylations and intramolecular Mitsunobu lactonization.
The stereocontrolled total synthesis of altohyrtin A/spongistatin 1: The CD-spiroacetal segment
Paterson, Ian,Coster, Mark J.,Chen, David Y.-K.,Gibson, Karl R.,Wallace, Debra J.
, p. 2410 - 2419 (2007/10/03)
Stereocontrolled syntheses of the C16-C28 CD-spiroacetal subunit of altohyrtin A/spongistatin 1 (1), relying on kinetic and thermodynamic control of the spiroacetal formation, are described. The kinetic control approach resulted in a slight preference (60: 40) for the desired spiroacetal isomer. The thermodynamic approach allowed ready access to the desired spiroacetal 2 by acid-promoted equilibration, Chromatographic separation of the C23 epimers and resubjection of the undesired isomer to the equilibration conditions. This scalable synthetic sequence provided multi-gram quantities of 2, thus enabling the successful completion of the total synthesis of altohyrtin A/spongistatin 1, as reported in Part 4 of this series. The Royal Society of Chemistry 2005.
Radical cyclization of β-alkoxymethacrylates: Expedient synthesis of (+)-methyl nonactate
Lee, Eun,Choi, Seung Jib
, p. 1127 - 1128 (2008/02/09)
(matrix presented) Radical cyclization of the β-alkoxymethacrylate obtained from 5-benzyloxy-1-iodohexan-3-ol led to the stereoselective preparation of the benzyl ether of (+)-methyl nonactate, demonstrating "2,5-cis" selectivity in the radical cyclizatio
A synthesis of (+)-nonactic acid by means of the sulfur-ylide rearrangement
Honda,Ishige,Araki,Akimoto,Hirayama,Tsubuki
, p. 79 - 88 (2007/10/02)
(+)-Nonactic acid (1) has been synthesized by employing a condensation of the tetrahydro-2-furanthione (9) with dimethyl α-diazomalonate in the presence of rhodium acetate as a key reaction.
Total Synthesis of (-)-Colletol
Keck, Gary E.,Murry, Jerry A.
, p. 6606 - 6611 (2007/10/02)
The first total synthesis of the unsymmetrical bis-macrolide (-)-colletol is described.The synthesis involves a Lewis acid mediated addition of triphenylallylstannane to aldehyde 14 to set the C12 stereochemistry.The penultimate step utilized m
CONCERNING THE ROLE OF LEWIS ACIDS IN CHELATION CONTROLLED ADDITION TO CHIRAL ALKOXY ALDEHYDES
Reetz, M. T.,Kesseler, K.,Jung, A.
, p. 729 - 732 (2007/10/02)
Chiral α- and β-alkoxy aldehydes react stereoselectively with various C-nucleophiles in th epresence of Lewis acids to provide chelation controlled adducts.
ACYCLIC STEREOSELECTION. 20. HIGH DIASTEREOFACIAL SELECTIVITY IN THE STANNIC CHLORIDE MEDIATED REACTIONS OF ALLYLSILANES WITH CHIRAL α- AND β-ALKOXY ALDEHYDES.
Kiyooka, Syun-ichi,Heathcock, Clayton H.
, p. 4765 - 4768 (2007/10/02)
Stannic chloride is an effective catalyst for the reaction of allylsilanes with chiral α- and β-alkoxy aldehydes.In the case of α-alkoxy aldehyde 1, the diastereofacial preference is outstanding (>35:1).With β-alkoxy aldehydes 5 and 6, selectivity lower, but still quite acceptable (7-12:1).
