Silyl substituted furans in the stereoselective Birch reduction

Donohoe, Timothy J.; Guillermin, Jean-Baptiste; Calabrese, Andrew; Walter, Daryl S.

doi:10.1016/s0040-4039(01)01151-0

Cited by 24 publications

(9 citation statements)

References 10 publications

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“…[65] Thus, high levels of stereochemical control could be maintained, and both the TMS group and the chiral auxiliary could be easily removed with aqueous acid after the Birch reduction. [65] Thus, high levels of stereochemical control could be maintained, and both the TMS group and the chiral auxiliary could be easily removed with aqueous acid after the Birch reduction.…”

Section: Pregosin Et Al Developed the Use Of Meo-biphep 103mentioning

confidence: 99%

“…Pyrolysis at 180°C under reduced pressure afforded 2-methyl-2,3-dihydrofuran (10) in 73 % yield, which was further elaborated to eventually give trans-theaspirone (65). Pyrolysis at 180°C under reduced pressure afforded 2-methyl-2,3-dihydrofuran (10) in 73 % yield, which was further elaborated to eventually give trans-theaspirone (65).…”

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confidence: 99%

“…γ-Valerolactone (63) was reduced to the lactol with DI-BAL and esterified with benzoyl chloride to give 64 in 94 % yield. Pyrolysis at 180°C under reduced pressure afforded 2-methyl-2,3-dihydrofuran (10) in 73 % yield, which was further elaborated to eventually give trans-theaspirone (65).…”

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confidence: 99%

“…Donohoe further refined this approach by the incorporation of a temporary trimethylsilyl (TMS) group into the C-3 position. [65] Thus, high levels of stereochemical control could be maintained, and both the TMS group and the chiral auxiliary could be easily removed with aqueous acid after the Birch reduction. This work was recently applied to the formal synthesis of (-)-secosyrin 1 (135), a natural product isolated from pseudomonas syringae pv.…”

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Synthesis of Dihydrofurans Substituted in the 2‐Position

2005

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Many natural products and biologically active compounds contain the dihydrofuran subunit. Molecules incorporating either 2‐substituted, 2,2‐disubstituted 2,3‐ or 2,5‐dihydrofurans are widespread in the literature and represent key “molecular building blocks”. The preparation of substituted dihydrofurans remains a current challenge in organic synthesis and this microreview details the various routes employed for their synthesis in the literature to the end of 2004. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)

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Section: Pregosin Et Al Developed the Use Of Meo-biphep 103mentioning

confidence: 99%

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confidence: 99%

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confidence: 99%

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Synthesis of Dihydrofurans Substituted in the 2‐Position

2005

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“…[15][16][17][18][19] Although the strategy of Birch type reductive silylation has several drawbacks vs electrochemical silylation such as using metal reducing agents, and irregular yields, it has been well developed as one of useful methods for the formation of carbon-silicon bonds in both carbon and organosilicon chemistry. [20][21][22][23][24][25] Reductive polysilylations of PhSiCl3 and PhMeSiCl2 were reported to occur with excess lithium and Me3SiCl in THF to yield tetrasilylated cyclohexene (Ttc = tetrakis(trimethylsilyl)cyclohex-1-ene) derivatives. 7,8,11 However, to our knowledge, no investigation for the synthesis of a compound having two Ttc substituents on the same silicon atom has been appeared.…”

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confidence: 99%