Saturated oxygen heterocycles

Elliott, Mark

doi:10.1039/b201515n

Cited by 143 publications

(34 citation statements)

References 172 publications

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“…Both bicyclic products could be isolated and were characterized by one-and twodimensional NMR spectroscopy. The structural assignment is based on the value for the vicinal coupling constant 3 JA C H T U N G T R E N N U N G ( À HC=CH À ), which is 10.2 Hz for 9 and 6.3 Hz for 10, with both values being typical for dihydropyrans and dihydrofurans, respectively. [19] Another distinctive feature is the chemical shift value of the ether carbon atoms (9: 67.8 and 65.4 ppm; 10: 88.0 and 75.8 ppm).…”

Section: Regioselective Double Rcm: Fused Vs Dumbbelltype Bicyclic Smentioning

confidence: 99%

Synthesis of Dihydrofurans and Dihydropyrans with Unsaturated Side Chains Based on Ring Size‐Selective Ring‐Closing Metathesis

Schmidt

Nave

2007

Adv Synth Catal

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Enantiomerically pure 1,5-hexadiene-3,4-diol, derived from d-mannitol in a few steps, may serve as a starting material for enantiopure dihydropyrans and dihydrofurans bearing an unsaturated side chain which is amenable for further synthetic transformations. The synthesis relies on a ring sizeselective ring-closing metathesis reaction of a triene. Most likely, a catalyst-directing effect of an allylic hydroxy group is responsible for the selectivity.

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Section: Regioselective Double Rcm: Fused Vs Dumbbelltype Bicyclic Smentioning

confidence: 99%

Synthesis of Dihydrofurans and Dihydropyrans with Unsaturated Side Chains Based on Ring Size‐Selective Ring‐Closing Metathesis

Schmidt

Nave

2007

Adv Synth Catal

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“…[1] A plethora of methods have been developed to construct these systems which are difficult to synthesize by "classical" methods due the unfavourable entropy and enthalpy of activation associated with the forming medium ring.…”

Section: Introductionmentioning

confidence: 99%

“…[1] The C 15 -halogenated acetogenins isolated from the Laurencia species of red algae, and those marine organisms which feed on L. sp., have frequently been used as a testing ground for new methods developed for the construction of medium-ring ethers.…”

Section: Introductionmentioning

confidence: 99%

“…Thus, exposure of (+)-6 to DBU caused isomerization to the allylic alcohol (À)-7 ([a] 21 D = À25.8 (c = 2.9 in CHCl 3 )). The enantiomeric excess of the allylic alcohol (À)-7, and hence of the epoxide (+)-6, was determined by 1 H NMR spectroscopy by using the chiral-shift reagent [(+)-EuA C H T U N G T R E N N U N G (hfc) 3 ] (hfc = 3-(heptafluoropropylhydroxymeth- www.chemeurj.org ylene)camphorate); the enantiomeric excess was confirmed by Moshers ester analysis of a later synthetic intermediate, the lactone (À)-8 (vide infra). By analogy with Tamms observations, [19] the epoxide (+)-6 was presumed to have the (3R,4R)-configuration which was confirmed by comparison of the optical rotation of the allylic alcohol (À)-7 with the known antipode [20] (Scheme 2).…”

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confidence: 99%

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Synthesis of (+)‐Obtusenyne

Mak

Curtis

Payne

et al. 2008

Chemistry A European J

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An enantioselective synthesis of the halogenated medium-ring ether natural product (+)-obtusenyne is reported which uses the ring expansion of a seven-membered ketene acetal by means of a Claisen rearrangement to construct the core nine-membered oxygen heterocycle. The trans substituents across the ether linkage were established by using a transition-metal-catalyzed intramolecular hydrosilation reaction of an exo-cyclic enol ether. In addition, a formal synthesis of ent-obtusenyne from 2-deoxy-D-ribose is reported. A number of interesting points regarding the chemistry of medium-ring oxygen heterocycles are highlighted.

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“…These motifs can also be found in various monocyclic and polycyclic compounds, cyclic ethers or spiroketals [1][2][3][4][5][6][7]. (-)-Centrolobine (1) is a six membered heterocyclic natural product in which tetrahydropyran ring is present in syn-fashion.…”

Section: Introductionmentioning

confidence: 99%

Lipase-Catalyzed Resolution of 1-[4-(Benzyloxy)phenyl]hex-5-en-3-ol: Synthesis of (-)-Centrolobine

Tadiparthi¹,

Raghavendra²,

Kamal³

2017

Asian J. Chem.

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A practical and efficient method for the preparation of homoallylic alcohol and its successful enzymatic resolution has been developed. This lipase-catalyzed resolution process has been optimized with respect to different lipases and solvents. Moreover, Mitsunobu strategy has been applied to recover the unwanted isomer. Further optically enriched homoallylic alcohol has been employed for the synthesis of (-)-centrolobine.

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Saturated oxygen heterocycles

Cited by 143 publications

References 172 publications

Synthesis of Dihydrofurans and Dihydropyrans with Unsaturated Side Chains Based on Ring Size‐Selective Ring‐Closing Metathesis

Synthesis of Dihydrofurans and Dihydropyrans with Unsaturated Side Chains Based on Ring Size‐Selective Ring‐Closing Metathesis

Synthesis of (+)‐Obtusenyne

Lipase-Catalyzed Resolution of 1-[4-(Benzyloxy)phenyl]hex-5-en-3-ol: Synthesis of (-)-Centrolobine

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