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Literature DB >> 10930287

Catalyzed asymmetric diels-alder reaction of benzoquinone. Total synthesis of (-)-ibogamine.

Abstract

The Diels-Alder addition of diene 2 with benzoquinone catalyzed by (S)-BINOL-TiCl(2) produced cycloadduct 5 in >65% yield and 87% ee. The cycloadduct was transformed into (-)-ibogamine in nine steps (10% overall yield from benzoquinone). A model for the transition state leading to 5 is proposed.

Entities: Chemical

Mesh：

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Year: 2000 PMID： 10930287 DOI： 10.1021/ol0001463

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

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Cited

7 in total

1. Catalytic, asymmetric reactions of ketenes and ketene enolates.

Authors: Daniel H Paull; Anthony Weatherwax; Thomas Lectka
Journal: Tetrahedron Date: 2009-08-22 Impact factor: 2.457

2. Further studies of intramolecular Michael reactions of nitrosoalkenes for construction of functionalized bridged ring systems.

Authors: Praveen Kumar; Puhui Li; Ilia Korboukh; Tony L Wang; Hemant Yennawar; Steven M Weinreb
Journal: J Org Chem Date: 2011-02-28 Impact factor: 4.354

3. Asymmetric transformations of achiral 2,5-cyclohexadienones.

Authors: Kyle A Kalstabakken; Andrew M Harned
Journal: Tetrahedron Date: 2014-12-23 Impact factor: 2.457

4. Visible Light-Promoted Beckmann Rearrangements: Separating Sequential Photochemical and Thermal Phenomena in a Continuous Flow Reactor.

Authors: Yuesu Chen; David Cantillo; C Oliver Kappe
Journal: European J Org Chem Date: 2019-03-08

Catalyzed asymmetric diels-alder reaction of benzoquinone. Total synthesis of (-)-ibogamine.

1. Catalytic, asymmetric reactions of ketenes and ketene enolates.

2. Further studies of intramolecular Michael reactions of nitrosoalkenes for construction of functionalized bridged ring systems.

3. Asymmetric transformations of achiral 2,5-cyclohexadienones.

4. Visible Light-Promoted Beckmann Rearrangements: Separating Sequential Photochemical and Thermal Phenomena in a Continuous Flow Reactor.

5. Design of an Organocatalytic Asymmetric (4 + 3) Cycloaddition of 2-Indolylalcohols with Dienolsilanes.

Review 6. The iboga enigma: the chemistry and neuropharmacology of iboga alkaloids and related analogs.

7. Enantioselective synthesis of Iboga alkaloids and vinblastine via rearrangements of quaternary ammoniums.