Hydrolytic ring-opening of α,β-epoxysilanes to α,β-dihydroxysilanes

Hudrlik, Paul F.; Arcoleo, J.P.; Schwartz, Robert H.; Misra, Raj N.; Rona, Robert J.

doi:10.1016/s0040-4039(01)92701-7

Cited by 25 publications

(10 citation statements)

References 13 publications

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“…Capitalizing on the effects of a silyl group attached directly to an epoxide, studied in detail by Hudrlik [188,189] and Paquette [190], Jamison developed an iterative approach to the synthesis of trans-fused oligo(tetrahydropyran) fragments (Scheme 15.14c) [18]. In contrast to cyclization of epoxysulfones, in which the sulfone deactivates the undesired site of epoxide opening, silyl groups stabilize positive charge in the transition state leading to 6-endo epoxide opening.…”

Section: Epoxide-opening Cascades In the Synthesis Of Polycyclic Polymentioning

confidence: 99%

Biomimetic Synthesis of Polyether Natural Products via Polyepoxide Opening

Vilotijević

Jamison

2011

Biomimetic Organic Synthesis

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Section: Epoxide-opening Cascades In the Synthesis Of Polycyclic Polymentioning

confidence: 99%

Biomimetic Synthesis of Polyether Natural Products via Polyepoxide Opening

Vilotijević

Jamison

2011

Biomimetic Organic Synthesis

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“…The structural effects of a silyl group attached directly to an epoxide have been studied in detail by Hudrlik [232][233][234] and Paquette, [235] and the electronic properties of these substituents have been exploited in epoxide-opening reactions of epoxysilanes. For example, Heffron and Jamison developed an iterative approach to the synthesis of trans-fused oligotetrahydropyran fragments in this fashion (Scheme 29).…”

Section: Iterative Approachesmentioning

confidence: 99%

Epoxide‐Opening Cascades in the Synthesis of Polycyclic Polyether Natural Products

2009

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The group of polycyclic polyether natural products is of special interest due to the fascinating structure and biological effects displayed by its members. The latter includes potentially therapeutic antibiotic, antifungal, and anticancer properties, as well as extreme lethality. The polycyclic structural features of this family can, in some cases, be traced to their biosynthetic origin, but in others that are less well understood, only to proposed biosynthetic pathways that feature dramatic, yet speculative, epoxide-opening cascades. In this review we summarize how such epoxide-opening cascade reactions have been used in the synthesis of polycyclic polyethers and related natural products.

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“…The structural effect of a silyl group attached directly to an epoxide has been studied in detail by Hudrlik [119–122] and Paquette [123]. These results have found application in the endo -selective intramolecular reactions of epoxysilanes developed in the Jamison group [124].…”

Section: Construction Of Tetrahydropyrans Via Endo-selective Epoximentioning

confidence: 99%

Synthesis of Marine Polycyclic Polyethers via Endo-Selective Epoxide-Opening Cascades

Vilotijević

Jamison

2010

Marine Drugs

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The proposed biosynthetic pathways to ladder polyethers of polyketide origin and oxasqualenoids of terpenoid origin share a dramatic epoxide-opening cascade as a key step. Polycyclic structures generated in these biosynthetic pathways display biological effects ranging from potentially therapeutic properties to extreme lethality. Much of the structural complexity of ladder polyether and oxasqualenoid natural products can be traced to these hypothesized cascades. In this review we summarize how such epoxide-opening cascade reactions have been used in the synthesis of ladder polyethers and oxasqualenoid natural products.

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Hydrolytic ring-opening of α,β-epoxysilanes to α,β-dihydroxysilanes

Cited by 25 publications

References 13 publications

Biomimetic Synthesis of Polyether Natural Products via Polyepoxide Opening

Biomimetic Synthesis of Polyether Natural Products via Polyepoxide Opening

Epoxide‐Opening Cascades in the Synthesis of Polycyclic Polyether Natural Products

Synthesis of Marine Polycyclic Polyethers via Endo-Selective Epoxide-Opening Cascades

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