Synthesis of 1,9‐Dideoxy‐pre‐axinellamine

Yamaguchi, Junichiro; Seiple, Ian B.; Young, Ian S.; O’Malley, Daniel P.; Maue, Michael; Baran, Phil S.

doi:10.1002/anie.200705913

Cited by 79 publications

(32 citation statements)

References 23 publications

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“…143-147 They then accomplished the syntheses of axinellamines ( 13 ) and massadines ( 14 ) in 2008. 148-150 Subsequently, they completed the total synthesis of the legendary natural product palau’amine ( 1 ) in 2010. 151 In 2011, the Baran group further reported the asymmetric synthesis of 1 , 13 , and 14 using an enantioselective Diels-Alder reaction to set up the absolute stereochemistry of these alkaloids.…”

Section: The Higher Order Pyrrole-imidazole Alkaloidsmentioning

confidence: 99%

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Syntheses of cyclic guanidine-containing natural products

Chen

2015

Tetrahedron

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Naturally occurring guanidine derivatives frequently display medicinally useful properties. Among them, the higher order pyrrole-imidazole alkaloids, the dragmacidins, the crambescidins/batzelladines, and the saxitoxins/tetradotoxins have stimulated the development of many new synthetic methods over the past decades. We provide here an overview of the syntheses of these cyclic guanidine-containing natural products.

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Section: The Higher Order Pyrrole-imidazole Alkaloidsmentioning

confidence: 99%

“…They first completed the synthesis of axinellamines ( 13 ), using an intramolecular aldol reaction to establish its central cyclopentyl core skeleton. 148,149 Specifically, ozonolysis of 64 obtained from a Diels-Alder reaction provided diketone 65 (Fig. 15).…”

Section: The Higher Order Pyrrole-imidazole Alkaloidsmentioning

confidence: 99%

Syntheses of cyclic guanidine-containing natural products

Chen

2015

Tetrahedron

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“…Given the exciting advances outlined above [26] and the recent arrival of completed total syntheses of complex oroidin dimers, [27] a creative solution to the synthetic problem posed by palau'amine amid other captivating and coveted natural products should be forthcoming in the near future.…”

Section: Outlook and Conclusionmentioning

confidence: 99%

Stereocontrolled Preparation of Fully Substituted Cyclopentanes: Relevance to Total Synthesis

Heasley

2009

Eur J Org Chem

101

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This Microreview aims to identify important advances in the asymmetric synthesis of fully substituted five-membered carbocyclic ring systems. Recent efforts directed towards the intricate and densely functionalized core substructures of three distinct classes of cyclopentane-based natural products will be examined. Strategies featuring high levels of stereocontrol and/or conciseness in the total number of synthetic steps

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“…In this case, an intramolecular conjugate addition took place after the formation of the enone moiety (Scheme 16). 240 v) The transformation of a diol into the corresponding dialdehyde has been performed using 2.4 equiv of IBX in MeCN at 80 ºC in the total synthesis of baconipyrone A, baconipyrone C, and siphonarin B (Scheme 16).…”

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confidence: 99%