Asymmetric 1,3-Dipolar Cycloaddition Reactions

Introduction Cationic domino reactions Anionic domino reactions Radical domino reactions Pericyclic domino reactions Photochemically induced domino processes Transition metal catalysis Domino reactions initiated by oxidation or reduction Enzymes in domino reactions Multicomponent reactions Special techniques in domino reactions

Domino Reactions in Organic Synthesis

Asymmetric fluorination, trifluoromethylation, and perfluoroalkylation reactions.

Update 1 of: Asymmetric Fluorination, Trifluoromethylation, and Perfluoroalkylation Reactions

Stereochemical Control in Organic-Synthesis Using Silicon-Containing Compounds

Stereoselective synthesis of (+)-testosterone via intramolecular 13-dipolar cycloadditxon of nitrile oxide

Highly enantiocontrolled total synthesis of (-)-protoemetinol

A novel approach to angular triquinanes via intramolecular 1,3-dipolar cycloaddition of nitrile oxide

An efficient and highly stereoselective approach toward the phomoidride family of natural products is described. The carbocyclic core structure was assembled using a tandem phenolic oxidation/Diels–Alder cycloaddition and a tandem 5-exo-trig/5-exo-trig radical cyclization to deliver an isotwistane intermediate that, upon a late-stage xanthate-initiated Grob fragmentation, furnishes the requisite bicyclo[4.3.1]decene.

Toward the synthesis of phomoidride D.

(1R*,2S*)-2-(2-Oxobut-3-enyl)-1-(1-oxoprop-2-enyl)-1,3,3-trimethylcyclopentane 5 was prepared stereoselectively from 4,4-dimethylcyclopent-2-en-1-one 6 and then converted into the conjugated silyl enol ether 17. Intramolecular cycloaddition of 17, followed by base-catalysed equilibration, provided (1S*,2R*,7R*,9R*)-3-tert-butyldimethylsiloxy-9,12,12-trimethyltricyclo[7.3.0.0]dodec-3-en-8-one 18a, which was transformed, after contraction of the cyclohexene ring, into the synthetic intermediate 32 for (±)-Δ9(12)-capnellene 1.

Stereoselective construction of cis-transoid-cis-tricyclo[7.3.0.0]dodecanes by an intramolecular Diels–Alder reaction: a formal total synthesis of (±)-Δ9(12)-capnellene

Nobuaki Taniguchi

Papers

Stereoselective synthesis of (+)-testosterone via intramolecular 13-dipolar cycloadditxon of nitrile oxide

Highly enantiocontrolled total synthesis of (-)-protoemetinol

A novel approach to angular triquinanes via intramolecular 1,3-dipolar cycloaddition of nitrile oxide

Toward the synthesis of phomoidride D.

Stereoselective construction of cis-transoid-cis-tricyclo[7.3.0.0]dodecanes by an intramolecular Diels–Alder reaction: a formal total synthesis of (±)-Δ9(12)-capnellene