One‐Pot Stereoselective Double Intramolecular Oxymercuration: Synthesis of Four Isomers of an Unsymmetrical Bis‐Tetrahydrofuran Ring System

Mohapatra, Debendra K.; Naidu, P. Ramesh; Reddy, D. Narasimha; Nayak, Smita; Mohapatra, Seetaram

doi:10.1002/ejoc.201000861

Cited by 18 publications

(10 citation statements)

References 40 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…As depicted in Scheme , the journey started with the synthesis of the key C -allyl glycosides 8 and 9 . The known epoxide 5 was prepared from d -glucose in seven steps following the reported procedures . The selective opening of epoxide 5 with cuprate derived from n -BuLi at 40 °C followed by benzylation of C5–OH in the resulting compound 6 gave the benzyl ether 7 .…”

Section: Resultssupporting

confidence: 74%

“…The known epoxide 5 was prepared from d -glucose in seven steps following the reported procedures. 15 The selective opening of epoxide 5 with cuprate derived from n -BuLi at 40 °C followed by benzylation of C5–OH in the resulting compound 6 gave the benzyl ether 7 . 16 Next, compound 7 was subjected to C -allylation employing the standard conditions that involve the use of allylTMS (5 equiv) and BF 3 ·Et 2 O (3 equiv) in dichloromethane at 0 °C to obtain α- and β- C -allyl glycosides 8 and 9 , respectively, in 81% yield in a 2:7 ratio.…”

Section: Resultsmentioning

confidence: 99%

See 1 more Smart Citation

Total Synthesis of (+)-Petromyroxol, (−)-iso-Petromyroxol, and Possible Diastereomers

et al. 2020

View full text Add to dashboard Cite

The total synthesis of (+)-petromyroxol ( 1 ) and its seven diastereomers including the (−)- iso -petromyroxol ( 2 ) is described. The employed strategy involves the use of easily available C5-epimeric epoxides 5 and 5′ and nonselective anomeric C1-allylation, proceeding with or without inversion at C2, thereby giving the possibility of synthesizing all possible diastereomers. Extensive two-dimensional (2D) NMR analyses of all eight diastereomers have been carried out to assign the chemical shifts of the central carbons and the corresponding attached hydrogens and to learn how the C/H-chemical shifts of the tetrahydrofuran ring were influenced by the adjacent centers.

show abstract

Section: Resultssupporting

confidence: 74%

Section: Resultsmentioning

confidence: 99%

Total Synthesis of (+)-Petromyroxol, (−)-iso-Petromyroxol, and Possible Diastereomers

et al. 2020

View full text Add to dashboard Cite

show abstract

“…56 One recent example of a synthesis using mercuroetherification was also achieved by Mohapatra and co-workers, using mercury (II) acetate. 57 …”

Section: Scheme 17 : Unexpected Cyclization Toward the Synthesis Of Lmentioning

confidence: 97%

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

et al. 2016

View full text Add to dashboard Cite

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.

show abstract

“…Keeping the installation of the chloro group by the S N 2 displacement of the C(2)-hydroxyl group, the corresponding bromo-substituted bis -furanyl C -glycoside 4β was intended from the methyl furanosides 5 through a bromo-etherification followed by C -glycosidation. The synthesis of the advanced intermediate 5 was planned from the easily accessible epoxide 6 by a simple synthetic maneuver …”

mentioning

confidence: 99%

“…The synthesis of the key intermediate 5 started with the preparation of the epoxide 6 from glucose diacetonide 7 in 5 steps according to the literature procedure and opened with 1-butyne according to the established procedure (Scheme ). The resulting propargyl alcohol 8 was selectively reduced to E -olefin 9 under Birch conditions employing Li and liquid NH 3 at −50 °C.…”

mentioning

confidence: 99%

Total Synthesis of Notoryne

2018

View full text Add to dashboard Cite

The structure of notoryne comprises a halogenated 2,2'-bifuranyl moiety along with a terminal cis-enyne unit. In this work, we document the first total synthesis of notoryne, confirming its assigned relative and absolute configurations. The devised route comprises a glucose diacetonide-derived chiral pool intermediate as the starting point and 5- endo bromo-etherification for making the key bis-furan unit, anomeric C-allylation, as well as a relay cross-metathesis to install the cis-enyne unit.

show abstract

One‐Pot Stereoselective Double Intramolecular Oxymercuration: Synthesis of Four Isomers of an Unsymmetrical Bis‐Tetrahydrofuran Ring System

Cited by 18 publications

References 40 publications

Total Synthesis of (+)-Petromyroxol, (−)-iso-Petromyroxol, and Possible Diastereomers

Total Synthesis of (+)-Petromyroxol, (−)-iso-Petromyroxol, and Possible Diastereomers

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

Total Synthesis of Notoryne

Contact Info

Product

Resources

About