Alkoxide precoordination to rhodium enables stereodirected catalytic hydrogenation of a dihydrofuranol precursor of the C29-40 F/G sector of pectenotoxin-2

Peng, Xiaowen; Bondar, Dmitriy; Paquette, Leo A.

doi:10.1016/j.tet.2004.06.142

Cited by 40 publications

(14 citation statements)

References 44 publications

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“…4. The level of production of (XIII) provides suggestive indication that hydroxyl-directed hydrogenation is unable to operate at the heightened levels customarily observed (Brown, 1987;Crabtree & Davis, 1986;Peng et al, 2004;Stork & Kahne, 1983).…”

Section: S1 Commentmentioning

confidence: 80%

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(+)-(1S,5R,10S)-11,11-Dimethyl-4-oxatricyclo[8.4.0.0^1,5]tetradecane-3,12-dione

et al. 2007

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The title compound, C15H22O3, was prepared via amino-acid-promoted Robinson annulation followed by tandem Pd/C-mediated hydrogenation and oxidative cyclization. This product was instrumental in determining the feasibility of a stereocontrolled hydrogenation in which the directing hydroxyl group is adjacent to the 6–7-ring network and its olefinic component. The asymmetric unit consists of a single molecule with normal geometric parameters. The absolute configuration was assigned based on the known enantiomeric prescursor. Intermolecular C—H...O interactions link each molecule with four neighboring molecules

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Section: S1 Commentmentioning

confidence: 80%

“…For related chemistry, see: Brown (1987); Crabtree & Davis (1986) ;Inomata et al (2005), Nagamine et al (2007); Peng et al (2004); Stork & Kahne (1983). For related literature on geometry, see: Allen et al (1987); Desiraju & Steiner (1999); Steiner & Saenger (1992); Taylor & Kennard (1982).…”

Section: Related Literaturementioning

confidence: 99%

(+)-(1S,5R,10S)-11,11-Dimethyl-4-oxatricyclo[8.4.0.0^1,5]tetradecane-3,12-dione

et al. 2007

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“…A one-pot DIBAL-H reduction followed by Lewis acid mediated cyanation gave a mixture of desired and undesired cyanides 95 and 96 in a 1:1 ratio; the undesired cyanide 95 could be converted into a 2:3 ratio of desired and undesired cyanides by deprotonation with LiHMDS followed by aqueous workup. DIBAL-H/nBuLi reduction of cyanide to aldehyde, Horner-Wadsworth-Emmons reaction, [62] and ruthenium-catalyzed oxidative cleavage of the terminal olefin [63] afforded the keto aldehyde 98 in good Scheme 7. Nicolaous formal synthesis of (AE )-platensimycin.…”

Section: Yamamotos Formal Synthesis Of (à)-Platensimycinmentioning

confidence: 99%

“…A one‐pot DIBAL‐H reduction followed by Lewis acid mediated cyanation gave a mixture of desired and undesired cyanides 95 and 96 in a 1:1 ratio; the undesired cyanide 95 could be converted into a 2:3 ratio of desired and undesired cyanides by deprotonation with LiHMDS followed by aqueous workup. DIBAL‐H/ n BuLi reduction of cyanide to aldehyde, Horner–Wadsworth–Emmons reaction,62 and ruthenium‐catalyzed oxidative cleavage of the terminal olefin63 afforded the keto aldehyde 98 in good yield. Then, the key intramolecular Robinson annulation was accomplished using L ‐proline as the matched chiral element to mediate the intramolecular Michael addition, followed by aldol condensation with sodium hydroxide to furnish the core structure of platensimycin and its C‐9 epimer in a 5:1 ratio in favor of the desired one.…”

Section: Total and Formal Synthesis Of Platensimycinmentioning

confidence: 99%

Discovery and Syntheses of “Superbug Challengers”—Platensimycin and Platencin

Palanichamy

Kaliappan

2010

Chemistry An Asian Journal

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Bacteria have developed resistance to almost all existing antibiotics known today and this has been a major issue over the last few decades. The search for a new class of antibiotics with a new mode of action to fight these multiply-drug-resistant strains, or "superbugs", allowed a team of scientists at Merck to discover two novel antibiotics, platensimycin and platencin using advanced screening strategies, as inhibitors of bacterial fatty acid biosynthesis, which is essential for the survival of bacteria. Though both these antibiotics are structurally related, they work by slightly different mechanisms and target different enzymes conserved in the bacterial fatty acid biosynthesis. This Focus Review summarizes the synthetic and biological aspects of these natural products and their analogues and congeners.

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“…A synthesis of an FG-ring fragment has previously been reported from the laboratories of Murai et al 15,16 in which the main backbone of the FG rings was prepared by reaction of an anion generated from a chiral a-lithio tetrahydrofuranyl ring, representing the F ring, with a five-carbon aldehyde fragment. Studies toward the F ring have also emanated from the work of Paquette et al 17,18 who employed an elegant hydroxyl-directed hydrogenation of a dihydrofuran to generate the desired chirality present in the tetrahydrofuran F ring.…”

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confidence: 99%