Stereoselective Synthesis of 4-O-Tosyltetrahydropyrans via Prins Cyclization Reaction of Enol Ethers

Intramolecular cyclization of enol ethers mediated by para-toluenesulfonic acid leads to substituted tetrahydropyrans in good to moderate yields. The reaction is diastereoselective.

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Stereoselective synthesis of O-tosyl azabicyclic derivatives via aza Prins reaction of endocyclic N-acyliminium ions: application to the total synthesis of (±)-epi-indolizidine 167B and 209D

Organic & Biomolecular Chemistry ◽

10.1039/c4ob01130a ◽

2014 ◽

Vol 12 (36) ◽

pp. 7026-7035 ◽

Cited By ~ 28

Author(s):

Anil K. Saikia ◽

Kiran Indukuri ◽

Jagadish Das

Keyword(s):

Total Synthesis ◽

Stereoselective Synthesis ◽

Cyclization Reaction ◽

Diastereoselective Synthesis ◽

Prins Reaction ◽

Prins Cyclization ◽

Acyliminium Ions

A diastereoselective synthesis of 4-O-tosyl piperidine containing azabicyclic derivatives has been established via Prins cyclization reaction. This protocol has been applied for the total synthesis of (±)-epi-indolizidine 167B and 209D.

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Stereoselective Synthesis of 3-Fluorotetrahydrofuran-3-carboxylate Derivatives via the Intramolecular Cyclization Reaction of Erythro- and Threo-α-allylated α-Fluoro-β-hydroxy Esters.

ChemInform ◽

10.1002/chin.200240116 ◽

2002 ◽

Vol 33 (40) ◽

pp. 116-116

Author(s):

Kazuhide Mima ◽

Kei Sato ◽

Takashi Ishihara ◽

Tsutomu Konno ◽

Hiroki Yamanaka

Keyword(s):

Intramolecular Cyclization ◽

Stereoselective Synthesis ◽

Cyclization Reaction ◽

Hydroxy Esters

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Stereoselective synthesis of 3-fluorotetrahydrofuran-3-carboxylate derivatives via the intramolecular cyclization reaction of erythro- and threo-α-allylated α-fluoro-β-hydroxy esters

Journal of Fluorine Chemistry ◽

10.1016/s0022-1139(02)00005-2 ◽

2002 ◽

Vol 115 (1) ◽

pp. 55-65 ◽

Cited By ~ 3

Author(s):

Kazuhide Mima ◽

Kei Sato ◽

Takashi Ishihara ◽

Tsutomu Konno ◽

Hiroki Yamanaka

Keyword(s):

Intramolecular Cyclization ◽

Stereoselective Synthesis ◽

Cyclization Reaction ◽

Hydroxy Esters

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Synthetic Studies on Cyclocitrinol: Construction of the ABC Ring System Based on Epoxy-Nitrile Cyclization

Synlett ◽

10.1055/a-1334-6100 ◽

2020 ◽

Author(s):

Kazuto Sato ◽

Keiji Tanino

Keyword(s):

Intramolecular Cyclization ◽

Ring Opening ◽

Model Compound ◽

Stereoselective Synthesis ◽

Ring System ◽

Cyclization Reaction ◽

Ring Opening Reaction ◽

Synthetic Studies ◽

Highly Strained

The stereoselective synthesis of a model compound containing the ABC ring system of cyclocitrinol was accomplished. After connecting a C-ring allyltitanium segment with an A ring bicyclo[4.1.0]heptanone segment, the seven-membered B ring moiety was constructed by an intramolecular cyclization reaction of an epoxy nitrile. The enone moiety was introduced through an oxidative decyanation reaction, and the bicyclo[4.4.1]undecane skeleton with the highly strained olefin moiety was formed through a ring-opening reaction of the bicyclo[4.1.0]heptane substructure.

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