Photocyclization of α,β-unsaturated amide aldehydes synthesis of jatropham

Dittami, James P.; Xu, Feng; Hua, Qi; Martin, Matthew W.; Bordner, Jon; Decosta, D. L.; Kiplinger, Jeffrey P.; Reiche, P.; Ware, R.

doi:10.1016/0040-4039(95)00780-g

Cited by 34 publications

(12 citation statements)

References 20 publications

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“…As given in the retrosynthetic analysis and based on the preference in literature for the preparation of jatropham by photocyclization [ 22 ], intramolecular cyclization of the aldehyde 27 was considered for the preparation of gigantamide A ( 7 ). The aldehyde 27 in turn could be prepared from dasyclamide ( 6 ).…”

Section: Resultsmentioning

confidence: 99%

Total synthesis of (+)-grandiamide D, dasyclamide and gigantamide A from a Baylis–Hillman adduct: A unified biomimetic approach

Satish¹,

Saravanakumar²

2014

Beilstein J. Org. Chem.

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Section: Resultsmentioning

confidence: 99%

Total synthesis of (+)-grandiamide D, dasyclamide and gigantamide A from a Baylis–Hillman adduct: A unified biomimetic approach

Satish¹,

Saravanakumar²

2014

Beilstein J. Org. Chem.

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“…[133] Dabei wurde ausgehend von Keton 84 durch eine Spinzentrenverschiebung [134] Analog zur klassischen Norrish-Yang-Cyclisierung können auch a,b-ungesättigte g-Ketoamide zu N-Alkylpyrrolidinonen umgesetzt werden, [136] was in einer Totalsynthese von (AE )-Jatropham angewendet wurde. [137] 4. Norrish-Typ-I-Spaltungen…”

Section: Aufsätzeunclassified

Photochemische Reaktionen als Schlüsselschritte in der Naturstoffsynthese

2011

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Photochemische Reaktionen bereichern in signifikanter Weise das Repertoire zur Knüpfung von Kohlenstoff‐Kohlenstoff‐Bindungen und machen ungewöhnliche, auf herkömmlichem Weg nicht erhältliche Molekülgerüste zugänglich. In diesem Aufsatz werden die wichtigsten Umsetzungen der Photochemie vorgestellt, die auf breiter Front Einzug in die Naturstoffsynthese gehalten haben. Beispielhaft werden einzelne Totalsynthesen diskutiert, wobei besonderes Augenmerk auf den photochemischen Schlüsselschritt sowie dessen Stereoselektivität gerichtet ist. Dabei wird das photochemisch erzeugte Molekül in Relation zur Struktur des Naturstoffs gebracht, und Folgereaktionen werden, wo notwendig, illustriert und klassifiziert.

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“…In analogy to the classic Norrish–Yang cyclization, α,β‐unsaturated γ‐ketoamides can be transformed into N ‐alkyl pyrrolidinones 136. This reaction was employed in the total synthesis of (±)‐jatropham 137…”

Section: Norrish–yang Cyclizationsmentioning

confidence: 99%

Corrosion News

2007

Materials & Corrosion

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Photochemical reactions contribute in a significant way to the existing repertoire of carbon–carbon bond‐forming reactions by allowing access to exceptional molecular structures that cannot be obtained by conventional means. In this Review, the most important photochemical transformations that have been employed in natural product synthesis are presented. Selected total syntheses are discussed as examples, with particular attention given to the photochemical key step and its stereoselectivity. The structural relationship between the photochemically generated molecule and the natural product is shown, and, where necessary, the consecutive reactions in the synthesis are illustrated and classified.

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Photocyclization of α,β-unsaturated amide aldehydes synthesis of jatropham

Cited by 34 publications

References 20 publications

Total synthesis of (+)-grandiamide D, dasyclamide and gigantamide A from a Baylis–Hillman adduct: A unified biomimetic approach

Total synthesis of (+)-grandiamide D, dasyclamide and gigantamide A from a Baylis–Hillman adduct: A unified biomimetic approach

Photochemische Reaktionen als Schlüsselschritte in der Naturstoffsynthese

Corrosion News

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