A two-directional approach to a (-)-dictyostatin C11-C23 segment: Development of a highly diastereoselective, kinetically-controlled Meerwein-Ponndorf-Verley reduction

Andrew K. Dilger; Vijay Gopalsamuthiram; Steven D. Burke

doi:10.1021/ja077336u

A two-directional approach to a (-)-dictyostatin C11-C23 segment: Development of a highly diastereoselective, kinetically-controlled Meerwein-Ponndorf-Verley reduction

Andrew K. Dilger
, Vijay Gopalsamuthiram
, Steven D. Burke

Chemistry (Twin Cities)

Research output: Contribution to journal › Article › peer-review

31 Scopus citations

Abstract

A three-step synthesis of a precursor to the C11-C23 segment of (-)-dictyostatin is described. The sequence features a sonication-assisted, enantioselective double hetero Diels-Alder (HDA) reaction catalyzed by Jacobsen's Cr(III) Schiff base catalyst, followed by a novel, highly diastereoselective Meerwein-Ponndorf-Verley (MPV) reduction of the hydropyranone subunits under kinetic control to yield the bis-(axial alcohol) 4. Generalized studies of both the HDA and MPV methodologies are also described.

Original language	English (US)
Pages (from-to)	16273-16277
Number of pages	5
Journal	Journal of the American Chemical Society
Volume	129
Issue number	51
DOIs	https://doi.org/10.1021/ja077336u
State	Published - Dec 26 2007

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10.1021/ja077336u

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A two-directional approach to a (-)-dictyostatin C11-C23 segment: Development of a highly diastereoselective, kinetically-controlled Meerwein-Ponndorf-Verley reduction. / Dilger, Andrew K.; Gopalsamuthiram, Vijay; Burke, Steven D.
In: Journal of the American Chemical Society, Vol. 129, No. 51, 26.12.2007, p. 16273-16277.

Research output: Contribution to journal › Article › peer-review

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abstract = "A three-step synthesis of a precursor to the C11-C23 segment of (-)-dictyostatin is described. The sequence features a sonication-assisted, enantioselective double hetero Diels-Alder (HDA) reaction catalyzed by Jacobsen's Cr(III) Schiff base catalyst, followed by a novel, highly diastereoselective Meerwein-Ponndorf-Verley (MPV) reduction of the hydropyranone subunits under kinetic control to yield the bis-(axial alcohol) 4. Generalized studies of both the HDA and MPV methodologies are also described.",

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AU - Burke, Steven D.

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AB - A three-step synthesis of a precursor to the C11-C23 segment of (-)-dictyostatin is described. The sequence features a sonication-assisted, enantioselective double hetero Diels-Alder (HDA) reaction catalyzed by Jacobsen's Cr(III) Schiff base catalyst, followed by a novel, highly diastereoselective Meerwein-Ponndorf-Verley (MPV) reduction of the hydropyranone subunits under kinetic control to yield the bis-(axial alcohol) 4. Generalized studies of both the HDA and MPV methodologies are also described.

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A two-directional approach to a (-)-dictyostatin C11-C23 segment: Development of a highly diastereoselective, kinetically-controlled Meerwein-Ponndorf-Verley reduction

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