The first example of a highly non-symmetric ozonolysis of a sugar derived norbornene system

Testero, Sebastián A.; Spanevello, Rolando A.; Kohli, Rakesh K.

doi:10.3998/ark.5550190.0004.a22

Cited by 5 publications

(1 citation statement)

References 5 publications

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“…Further studies by this group have addressed the issue of the fragmentation of the primary ozonide in carbohydrate-derived norbornene systems. They showed that, in participating solvents, the remote substitution is responsible for the regioselective fragmentation of the intermediate ozonide [129,130,131].…”

Section: Reactions Of Hex-2-enopyranosidesmentioning

confidence: 99%

A Survey of Recent Synthetic Applications of 2,3-Dideoxy-Hex-2-enopyranosides

et al. 2015

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Section: Reactions Of Hex-2-enopyranosidesmentioning

confidence: 99%

A Survey of Recent Synthetic Applications of 2,3-Dideoxy-Hex-2-enopyranosides

et al. 2015

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Towards the Synthesis of Massadine: A Unified Strategy for the Stereoselective Synthesis of the Carbocyclic C,D‐Ring Subunit

Breder¹,

Chinigo²,

Waltman³

et al. 2011

Chemistry A European J

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Massadine is a hexacyclic marine natural product, which belongs to the family of pyrrole-imidazole alkaloids. Herein, we describe a unified approach to the C,D-ring subunit of this sponge metabolite based on the exploitation of a norbornene scaffold for the stereocontrolled construction of massadine's carbon skeleton. Highlights of the sequence presented include the application of a stereospecific norbornyl rearrangement for facile introduction of an oxygen at the C7-position within the norbornene nucleus, a highly regioselective and end group differentiating ozonolytic scission of a C-C double bond, and an oxidative decarboxylation reaction for the installation of the hindered secondary C2-alcohol function. Furthermore, the iterative assembly of the two guanidine entities as well as the implementation of the spirocyclic junction between the C- and the D-rings are described. Collectively, these key transformations permit an entry to an appropriately functionalized carbon framework, which will serve as a starting point for our efforts toward the completion of the synthesis of massadine.

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End‐Group‐Differentiating Ozonolysis of Norbornene Systems To Afford Highly Substituted Cyclopentane Rings

et al. 2013

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The end‐group‐differentiating ozonolysis concept is discussed, with an emphasis on norbornene systems. Different remote functional groups in endo positions in norbornene derivatives are able to direct the primary ozonide fragmentation. By analysis of the factors affecting the regioselectivity, a rule to predict the direction of the primary ozonide rupture is formulated. These reactions give access to highly substituted cyclopentane rings and provide opportunities for their subsequent regioselective manipulation.

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The first example of a highly non-symmetric ozonolysis of a sugar derived norbornene system

Cited by 5 publications

References 5 publications

A Survey of Recent Synthetic Applications of 2,3-Dideoxy-Hex-2-enopyranosides

A Survey of Recent Synthetic Applications of 2,3-Dideoxy-Hex-2-enopyranosides

Towards the Synthesis of Massadine: A Unified Strategy for the Stereoselective Synthesis of the Carbocyclic C,D‐Ring Subunit

End‐Group‐Differentiating Ozonolysis of Norbornene Systems To Afford Highly Substituted Cyclopentane Rings

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