Synthesis of Rhazinilam: A Comparative Review of Forty Years of Synthetic Endeavors

Neier, Reinhard; Kholod, Inga; Vallat, Olivier; Buciumas, Ana‐Maria

doi:10.3987/rev-10-sr(e)2

Cited by 10 publications

(3 citation statements)

References 77 publications

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“…This alkaloid is a microtubule-disrupting agent that displays similar cellular effects to paclitaxel [72–73]. Because of its biological activities and potential pharmaceutical use, many groups have pursued its total synthesis [74–77], including a number of enantioselective syntheses [78–82]. …”

Section: Resultsmentioning

confidence: 99%

Formal total syntheses of classic natural product target molecules via palladium-catalyzed enantioselective alkylation

Liu¹,

Liniger²,

McFadden³

et al. 2014

Beilstein J. Org. Chem.

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SummaryPd-catalyzed enantioselective alkylation in conjunction with further synthetic elaboration enables the formal total syntheses of a number of “classic” natural product target molecules. This publication highlights recent methods for setting quaternary and tetrasubstituted tertiary carbon stereocenters to address the synthetic hurdles encountered over many decades across multiple compound classes spanning carbohydrate derivatives, terpenes, and alkaloids. These enantioselective methods will impact both academic and industrial settings, where the synthesis of stereogenic quaternary carbons is a continuing challenge.

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Section: Resultsmentioning

confidence: 99%

Formal total syntheses of classic natural product target molecules via palladium-catalyzed enantioselective alkylation

Liu¹,

Liniger²,

McFadden³

et al. 2014

Beilstein J. Org. Chem.

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“…The tetracyclic tetrahydroindolizine alkaloids rhazinal and rhazinilam have attracted considerable attention in the synthetic community as challenging targets for the evaluation of new synthetic methodologies. 1 A recent comprehensive review has summarized the numerous strategies devised for the synthesis of these alkaloids. 2 This article seeks to add a complementary approach to the existing routes that employs modern catalytic methodologies for the efficient synthesis of these natural products.…”

mentioning

confidence: 99%

“…Here, we report an efficient route to the Trauner intermediate 3 starting from 5. 6 Moreover, we investigated a protecting-group-free radical cyclization of intermediate 3 to form rhazinal (1), which would constitute a desirable key step for the construction of the nine-membered lactam.…”

mentioning

confidence: 99%