A Concise, Biomimetic Total Synthesis of (+)-Davanone

Morrison, Karen C.; Litz, Jonathan P.; Scherpelz, Kathryn P; Dossa, Paul D.; Vosburg, David A.

doi:10.1021/ol900697w

Cited by 21 publications

(12 citation statements)

References 24 publications

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“…[81] Neben Estergruppen wurden auch andere Funktionalitäten, wie Amide [82] und Acylazide, [83] durch diese NHC-Redoxmethode erhalten. [88] Die Behandlung des a,b-Epoxyaldehyds 114 mit dem Thiazoliumsalz 113 und der Hünig-Base lçste eine Epoxidçffnung/Veresterung unter Bildung des anti-Diastereomers 115 in guter Ausbeute aus. [84] Diese Zwischenverbindungen erwiesen sich als ausgezeichnete konjugierte Akzep- toren.…”

Section: Nhc-katalysierte Redox-und Oxidationsprozesseunclassified

Anwendungen der Katalyse mit N‐heterocyclischen Carbenen in Totalsynthesen

et al. 2012

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Katalytische Umwandlungen mit N‐heterocyclischen Carbenen (NHCs) haben sich als effiziente Ansätze zum Aufbau komplexer Moleküle erwiesen. Seit der Veröffentlichung von Stetter 1975 zur Totalsynthese von cis‐Jasmon und Dihydrojasmon durch Carbenkatalyse hat sich die Anwendung von NHCs in der Totalsynthese, insbesondere in den letzten zehn Jahren, schnell verbreitet. Dieser Aufschwung ist zweifellos die Folge neuerer Entwicklungen bei NHC‐katalysierten Reaktionen, einschließlich der neuen Benzoin‐, Stetter‐, Homoenolat‐ und Aroylierungsprozesse. Die Umwandlungen ermöglichen ebenso typische wie auf Umpolung beruhende Bindungsbildungen und sind bereits als Schlüsselschritte in mehreren neuen Totalsynthesen aufgetreten. Dieser Kurzaufsatz beschreibt diese neuen Arbeiten und zeigt die verstärkten Einsatzmöglichkeiten der Carbenkatalyse in der Totalsynthese auf.

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Section: Nhc-katalysierte Redox-und Oxidationsprozesseunclassified

Anwendungen der Katalyse mit N‐heterocyclischen Carbenen in Totalsynthesen

et al. 2012

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“…[87] In 2009, Vosburg and co-workers reported a short total synthesis of (+)-davanone involving an epoxide-opening NHC reaction (Scheme 20). [88] The treatment of a,b-epoxyaldehyde 114 with the thiazolium salt 113 and Hunigs base triggered an epoxide opening/esterification to afford anti diastereomer 115 in good yield. A palladiumcatalyzed allylic O-alkylation, formation of the Weinreb amide, and Grignard addition furnished (+)-davanone (116) in only seven steps from geranyl acetate.…”

Section: Nhc-catalyzed Redox and Oxidative Processesmentioning

confidence: 99%

A Continuum of Progress: Applications of N‐Hetereocyclic Carbene Catalysis in Total Synthesis

et al. 2012

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N-Heterocyclic carbene (NHC) catalyzed transformations have emerged as powerful tactics for the construction of complex molecules. Since Stetter’s report in 1975 of the total synthesis of cis-jasmon and dihydrojasmon by using carbene catalysis, the use of NHCs in total synthesis has grown rapidly, particularly over the last decade. This renaissance is undoubtedly due to the recent developments in NHC-catalyzed reactions, including new benzoin, Stetter, homoenolate, and aroylation processes. These transformations employ typical as well as Umpolung types of bond disconnections and have served as the key step in several new total syntheses. This Minireview highlights these reports and captures the excitement and emerging synthetic utility of carbene catalysis in total synthesis.

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“…152 The sesquiterpene davanone exhibits antifungal and antispasmodic properties. 153 In 2009, Vosburg and co-workers 154 reported a synthetic strategy beginning with the known epoxy alcohol, available from geranyl acetate via allylic hydroxylation and Sharpless asymmetric epoxidation. 155 The prediction that the inherent diastereofacial preference of 199 would be to form trans-200 rather than the desired cis-configured product 156 prompted them to carry out the reaction with a range of chiral catalysts and reaction conditions.…”

Section: Scheme 42mentioning

confidence: 99%

Palladium-Mediated Total Synthesis of Bioactive Natural Products

Majumdar

Sinha

2013

Synthesis

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The search for efficient synthetic procedures for natural products, drugs, and materials with economical and ecological advantages is an important area of current interst in synthetic organic chemistry. We have made an attempt to summarize the progress made in this area since 2005. This article describes the syntheses of several natural products and drugs that employ multiple palladiumcatalyzed processes in either a sequential or a domino fashion. Palladium-Mediated Synthesis of Natural Products Containing a Sugar Moiety 4 Palladium-Mediated Synthesis of Marine Natural Products 5 Palladium-Mediated Synthesis of Amino Acids and Peptides 6 Palladium-Mediated Synthesis of Terpenoids 7 Miscellaneous Natural Products 8 Conclusion

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A Concise, Biomimetic Total Synthesis of (+)-Davanone

Cited by 21 publications

References 24 publications

Anwendungen der Katalyse mit N‐heterocyclischen Carbenen in Totalsynthesen

Anwendungen der Katalyse mit N‐heterocyclischen Carbenen in Totalsynthesen

A Continuum of Progress: Applications of N‐Hetereocyclic Carbene Catalysis in Total Synthesis

Palladium-Mediated Total Synthesis of Bioactive Natural Products

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