Sequencing Reactions with Samarium(II) Iodide

Molander, Gary A.; Harris, Christina R.

doi:10.1021/cr950019y

Cited by 1,038 publications

(293 citation statements)

References 137 publications

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“…With (Ϫ)-37 in hand, we turned to the critical oxidation event. As now expected, Parikh-Doering oxidation (57) of (Ϫ)-37 provided the corresponding aldehyde, which upon treatment with 35 mol % SmI 2 (58,59) in the presence of ␤-hydroxy ketone 34 (54) afforded a diastereomeric mixture of esters (38), effectively achieving oxidation at C(1); the yield for the two steps was again good (75%). Removal of the acetonide, also as expected, led to concomitant loss of the DEIPS group.…”

Section: Union Of the Northern And Southern Hemispheres Of (؉)-13-deomentioning

confidence: 52%

A unified approach to the tedanolides: Total synthesis of (+)-13-deoxytedanolide

Smith

Adams

Barbosa

et al. 2004

Proc. Natl. Acad. Sci. U.S.A.

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A unified approach for the construction of the potent marine antitumor agents (؉)-tedanolide (1) and (؉)-13-deoxytedanolide (2) is described. Highlights of the synthetic strategy include the development of a versatile bifunctional dithiane-vinyl iodide linchpin, the unorthodox use of the Evans-Tishchenko reaction, and a late-stage high-risk stereocontrolled introduction of the C(18,19) epoxide to achieve a total synthesis of (؉)-13-deoxytedanolide (2).

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Section: Union Of the Northern And Southern Hemispheres Of (؉)-13-deomentioning

confidence: 52%

A unified approach to the tedanolides: Total synthesis of (+)-13-deoxytedanolide

Smith

Adams

Barbosa

et al. 2004

Proc. Natl. Acad. Sci. U.S.A.

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“…A particular advantage of OPEN ACCESS these concepts is the huge increase in structural complexity facilitated by the use of even the simplest starting materials. This is also one of the driving factors for constant research advancements in this field [5][6][7][8][9][10][11][12][13][14][15][16][17].…”

Section: Introductionmentioning

confidence: 99%

Sequentially Palladium-Catalyzed Processes in One-Pot Syntheses of Heterocycles

Lessing

Müller

2015

Applied Sciences

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Sequentially Pd-catalyzed processes are excellent entries to heterocycle synthesis. The broad mechanistic variety combined with often very mild reaction conditions allow the concatenation of elementary organic and organometallic steps to novel sequences in the sense of one-pot domino and multicomponent reactions. Given the numerous opportunities of alkyne coordination and their Pd-mediated transformations, alkynylation and carbometallation play a key role, both for purely organometallic sequences as well as in those processes that are intercepted by cyclocondensation. Pd-catalyzed aminations also find more and more entry into novel heterocycle syntheses based upon this theme.

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“…2 This powerful and versatile one-electron transfer reductant is commercially available, but can also be conveniently prepared from samarium and diiodoethane or diiodomethane as a solution in THF. 3 Its properties and reactivity can further be modified by addition of catalysts 4 and by solvent additives.…”

Section: Introductionmentioning

confidence: 99%

Samarium Diiodide

Hölemann¹

2001

Synlett

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Sequencing Reactions with Samarium(II) Iodide

Cited by 1,038 publications

References 137 publications

A unified approach to the tedanolides: Total synthesis of (+)-13-deoxytedanolide

A unified approach to the tedanolides: Total synthesis of (+)-13-deoxytedanolide

Sequentially Palladium-Catalyzed Processes in One-Pot Syntheses of Heterocycles

Samarium Diiodide

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