Ring-Construction/Stereoselective Functionalization Cascade: Total Synthesis of Pachastrissamine (Jaspine B) through Palladium-Catalyzed Bis-cyclization of Bromoallenes

Inuki, Shinsuke; Yoshimitsu, Yuji; Oishi, Shinya; Fujii, Nobutaka; Ohno, Hiroaki

doi:10.1021/ol901904w

Cited by 52 publications

(13 citation statements)

References 39 publications

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“…This intermediate can be easily converted into pachastrissamine in a four-step sequence (Scheme 57). [156] This type of reaction may also be initiated by the bromopalladation of allenes. Alcaide et al have demonstrated that b,g-and g,d-allendiols 210 undergo intramolecular cyclization to a variety of enantiopure oxacycles 211 or 212 of different ring sizes in the presence of LiBr (Scheme 58).…”

Section: Cyclizations In the Presence Of Organic Halides Or Hxmentioning

confidence: 99%

Allenes in Catalytic Asymmetric Synthesis and Natural Product Syntheses

2012

Angew Chem Int Ed

1,001

259

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Allenes are the simplest class of cumulenes, with two contiguous C=C bonds, and show unique physical and chemical properties. These features make allenes particularly attractive in modern organic chemistry. In this Review, attention is paid to the advances made in catalytic asymmetric synthesis and natural product syntheses based on well-established reactions of allenes, such as propargylation, addition, cycloaddition, cycloisomerization, cyclization, etc., with or without catalysts. Their versatile reactivity, substituent-loading ability, axial to center chirality transfer, and controllable selectivity allow access to target molecules by unique and efficient approaches. The main topics in this Review are presented with selected examples from 2003 to 2011.

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Section: Cyclizations In the Presence Of Organic Halides Or Hxmentioning

confidence: 99%

Allenes in Catalytic Asymmetric Synthesis and Natural Product Syntheses

2012

Angew Chem Int Ed

1,001

259

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“…Ohno et al. used a similar cascade reaction for an elegant enantioselective total synthesis of jaspine B ( 150 , Scheme ) 66. Their approach, however, consists of a fully intramolecular system that furnishes fused bicycle 149 diastereoselectively in 88% yield as a single enantiomer.…”

Section: Versatile Building Blocks In Pd‐catalyzed Cascadesmentioning

confidence: 99%

Recent Advances in Palladium‐Catalyzed Cascade Cyclizations

2011

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The importance of palladium‐catalyzed cross coupling reactions in contemporary organic synthesis is undisputed and underlined by the Nobel Prize for Chemistry in 2010. In addition to the highly efficient cross coupling reactions for single CC bond construction, palladium‐catalyzed cascade processes involving multiple bond formations have emerged in recent years as valuable tools for the rapid synthesis of complex molecular scaffolds. This review presents an overview of the most relevant developments in this field, with a focus on the generation of diverse poly‐ and heterocyclic scaffolds. The generally well understood reactivity of palladium has allowed the discovery of many intriguing novel cascade processes, and the creativity of the synthetic community will undoubtedly lead to many more discoveries in the future.

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“…In anti-cancer assays, this novel sphingosine derivative proved to be the most potent compound against the A549 human lung carcinoma cell line isolated from the Jaspis genus. The combination of potent biological properties and relatively straightforward molecular structures has led to the development of a number of its synthetic preparations (Llaveria et al, 2011;Passiniemi & Koskinen, 2011;Yoshimitsu et al, 2011;Srinivas Rao & Venkateswara Rao, 2011;Urano et al, 2010;Salma et al, 2010;Inuki et al, 2009Inuki et al, , 2010Yoshimitsu et al, 2010;Vichare & Chattopadhyay, 2010;Canals et al, 2009;Enders et al, 2008;Abraham et al, 2008, and the articles cited in their review). The biological activities of numerous synthetic analogues and epimers have also been prepared and tested.…”

Section: Introductionmentioning

confidence: 99%

Aminohydroxylation of divinylcarbinol and its application to the synthesis of bicyclic hydroxypyrrolidine and aminotetrahydrofuran building blocks

et al. 2013

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Dedicated to Professor Štefan Toma on the occasion of his 75th birthdayAminohydroxylation of prochiral divinylcarbinol and subsequent Pd(II)-catalysed oxy-/amidocarbonylation of aminopentenediols is reported. The method was applied to the preparation of useful building blocks for syntheses of cytotoxic jaspines and glycosidase inhibitor DLX-homologues. The key intermediates, tetrahydrofuranolactones (l-arabino-II) and pyrrolidinolactones (l-arabino-IX and l-xylo-IX), were prepared in a short 2-step sequence from divinylcarbinol.

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Ring-Construction/Stereoselective Functionalization Cascade: Total Synthesis of Pachastrissamine (Jaspine B) through Palladium-Catalyzed Bis-cyclization of Bromoallenes

Cited by 52 publications

References 39 publications

Allenes in Catalytic Asymmetric Synthesis and Natural Product Syntheses

Allenes in Catalytic Asymmetric Synthesis and Natural Product Syntheses

Recent Advances in Palladium‐Catalyzed Cascade Cyclizations

Aminohydroxylation of divinylcarbinol and its application to the synthesis of bicyclic hydroxypyrrolidine and aminotetrahydrofuran building blocks

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