Development of a practical synthesis of novel, pyrrole-based HMG-CoA reductase inhibitors

Pfefferkorn, Jeffrey A.; Bowles, Daniel M.; Kissel, William S.; Boyles, David C.; Choi, Chulho; Larsen, Scott D.; Song, Yuntao; Sun, Kuai Lin; Miller, Steven R.; Trivedi, Bharat K.

doi:10.1016/j.tet.2007.06.005

Cited by 26 publications

(6 citation statements)

References 24 publications

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“…Unfortunately, many of these are long, multistep linear reaction sequences, often involving late and unselective functional group transformations and protection/deprotection steps with difficult purification procedures. Tedious preparation of chiral precursors, several synthetic steps, and a need of cryo-chemistry render these approaches less attractive (see Supporting Information for detailed discussion). ,,,− …”

mentioning

confidence: 99%

Lactone Pathway to Statins Utilizing the Wittig Reaction. The Synthesis of Rosuvastatin

Časar¹,

Steinbücher

Košmrlj

2010

J. Org. Chem.

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The first entry to statins via lactonized side chain is reported, exemplified by the synthesis of rosuvastatin. The key step is Wittig coupling of (2S,4R)-4-(tert-butyldimethylsilyloxy)-6-oxotetrahydro-2H-pyran-2-carbaldehyde and phosphonium salt of an appropriately functionalized pyrimidine heterocycle. One-pot deprotection and hydrolysis of the resulting 4-O-TBS rosuvastatin lactone provided rosuvastatin in high yield.

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mentioning

confidence: 99%

Lactone Pathway to Statins Utilizing the Wittig Reaction. The Synthesis of Rosuvastatin

Časar¹,

Steinbücher

Košmrlj

2010

J. Org. Chem.

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“…We were intrigued by the report of Pfefferkorn21 and coworkers at Pfizer in which case they were able to cleanly prepare ethyl N-isopropyl glycinate by reaction of isopropyl amine with ethyl α-bromoacetate without detecting any over alkylation products. As a result, we reacted (Scheme 3) two equivalents of 3,4-dimethoxyphenyethylamine ( 27 ) with ethyl α-bromoacetate in THF at room temperature.…”

Section: Resultsmentioning

confidence: 99%

The application of vinylogous iminium salt derivatives to efficient formal syntheses of the marine alkaloids lamellarin G trimethyl ether and ningalin B

et al. 2009

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Studies directed at the synthesis of lamellarin G trimethyl ether and ningalin B via vinylogous iminium salt derivatives are described. The successful strategy relies on the formation of a 2,4-disubstituted pyrrole or a 1,2,3,4-tetrasubstituted pyrrole from a vinylogous iminium salt or vinylogous iminium salt derivative. Subsequent transformations of these highly substituted pyrroles lead to efficient and regiocontrolled formal syntheses of the respective pyrrole containing natural products.

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“…[14,15] Interestingly, compounds 15 a-d are 2-(hydroxyalkyl)pyrroles, whereas compounds 15 e-i are 2-arylpyrroles. More vigorous conditions were required for tertiary allenol derivatives 6.…”

Section: Aldehydementioning

confidence: 99%

New Regiocontrolled Synthesis of Functionalized Pyrroles from 2‐Azetidinone‐Tethered Allenols

Alcaide

Almendros

Carrascosa

et al. 2007

Chemistry A European J

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A new one-pot approach to synthesize densely substituted racemic and enantiopure pyrroles from beta-lactams has been developed. The approach relies on the regiocontrolled cyclization of beta-allenamine intermediates derived from the ring opening of 2-azetidinone-tethered allenols. In this approach four points of diversity are introduced, one of which is the position of the allene moiety on the beta-lactam ring.

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Development of a practical synthesis of novel, pyrrole-based HMG-CoA reductase inhibitors

Cited by 26 publications

References 24 publications

Lactone Pathway to Statins Utilizing the Wittig Reaction. The Synthesis of Rosuvastatin

Lactone Pathway to Statins Utilizing the Wittig Reaction. The Synthesis of Rosuvastatin

The application of vinylogous iminium salt derivatives to efficient formal syntheses of the marine alkaloids lamellarin G trimethyl ether and ningalin B

New Regiocontrolled Synthesis of Functionalized Pyrroles from 2‐Azetidinone‐Tethered Allenols

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