Total Synthesis of (+)‐Oocydin A: Application of the Suzuki–Miyaura Cross‐Coupling of 1,1‐Dichloro‐1‐alkenes with 9‐Alkyl 9‐BBN

Roulland, Emmanuel

doi:10.1002/anie.200800585

Cited by 71 publications

(38 citation statements)

References 33 publications

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“…A onestep protection gave the 2,3-acetonide dimethyl ester, [20,21] which was then reduced [22] to provide diol 6. Mono protection of one alcohol with tBuMe 2 SiCl [23] followed by iodination [24] of the remaining hydroxy group gave 7 in an excellent 67 % overall yield over the four steps.…”

Section: Resultsmentioning

confidence: 99%

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Synthesis of an Acyclic C1–C11 Fragment of Peloruside B

et al. 2011

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Section: Resultsmentioning

confidence: 99%

“…Accurate masses were recorded on Mariner time-of-flight spectrometers. Compounds 6, [20][21][22] 7, [23,24] and 8 [24] were synthesized as described previously and spectroscopic data matched that of previously published spectra.…”

Section: Methodsmentioning

confidence: 99%

Synthesis of an Acyclic C1–C11 Fragment of Peloruside B

et al. 2011

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“…62 Later, Gandon and Roulland studied this reaction by DFT calculations. 63 The authors concluded that during the formation of a THF from a diol, the unreactive hydroxyl function controlled the stereochemical outcome of the reaction by complexing the palladium through the acetyl counteranion (Scheme 19).…”

Section: Scheme 18: Palladium Catalyzed Synthesis Of Thf From Phosphomentioning

confidence: 99%

Recent advances in the synthesis of tetrahydrofurans and applications in total synthesis

et al. 2016

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Mousseron. His research interests include the total synthesis of oxygenated cyclic and non cyclic metabolites of polyunsaturated fatty acids, mainly leukotrienes, iso-, phyto-and neuroprostanes, as well as dihydroxylated PUFAs and more recently lipophenols and the understanding of the role of such bioactive lipids and lipophenols by developing collaborations with chemists, biochemists, biologists and clinicians across the world. Jean-Marie Galano studied chemistry at Paul Cézanne Université Marseille and obtained his PhD under the supervision of Honoré Monti in 2001. He then moved to the University of Oxford to pursue a postdoctoral fellowship with David H. Hodgson on the development of new methods for the total synthesis of natural products. In October 2005 he joined the CNRS as a Chargé de Recherche at Université of Montpellier. His research focuses on the total synthesis and discovery of new lipid metabolites, and to discover their potential implications in human health. AbstractMany natural products contain tetrahydrofuran (THF) moieties. Those molecules, often biologically active, may be structurally diverse, e.g. cis or trans THF, mono-, di-, tri-or tetrasubstituted on the furan ring. Thus, the construction of THF is of great interest for the community of organic chemists; especially in developing new methodologies, and applying them in the total synthesis of natural products. The aim of this review is to report recent advances in the field of THF synthesis, as well as the application of these methods to the synthesis of bioactive compounds.

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“…77,78 The oxidation of a complex substrate bearing a primary alcohol has been described by Hirama and co-workers (Scheme 5). ROMPM, 114,115,118,183 ROBn, 80,90,104,106,110,124,191,192 ROTr, 180 ROMe, 94,101,107,113,192 RONPhth, 88 RON=CMe 2 , 88 ArOAllyl, 193 ArOMe, 108,130,131,192,194,195 ArOBn, 127,131 ArOTBS, 174 R 2 NBoc, 174,[194][195][196][197] 208 This IBX analogue generates only water during the oxidation, while DMP releases acetic acid. When DMP was applied the required keto ester was obtained in only 60%, with 40% of the starting lactone recovered (Scheme 6).…”

Section: 76mentioning

confidence: 99%