The total synthesis of the crinine alkaloid hamayne via a Pd[0]-catalyzed intramolecular Alder-ene reaction

Laurent Petit; Martin G. Banwell; Anthony C. Willis

doi:10.1021/ol2023938

The total synthesis of the crinine alkaloid hamayne via a Pd[0]-catalyzed intramolecular Alder-ene reaction

Laurent Petit, Martin G. Banwell^*, Anthony C. Willis

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

43 Citations (Scopus)

Abstract

The racemic form of the title alkaloid, 1, has been prepared in 13 steps from the ring-fused gem-dibromocyclopropane 7. Key transformations include the thermally induced electrocyclic ring-opening of compound 7, the Pd[0]-catalyzed intramolecular Alder-ene (IMAE) reaction of the derived sulfonamide (±)-12, and the conversion of the ensuing C-3a-arylhexahydroindole (±)-16 into (±)-hamayne via a Pictet-Spengler reaction.

Original language	English
Pages (from-to)	5800-5803
Number of pages	4
Journal	Organic Letters
Volume	13
Issue number	21
DOIs	https://doi.org/10.1021/ol2023938
Publication status	Published - 4 Nov 2011

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10.1021/ol2023938

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title = "The total synthesis of the crinine alkaloid hamayne via a Pd[0]-catalyzed intramolecular Alder-ene reaction",

abstract = "The racemic form of the title alkaloid, 1, has been prepared in 13 steps from the ring-fused gem-dibromocyclopropane 7. Key transformations include the thermally induced electrocyclic ring-opening of compound 7, the Pd[0]-catalyzed intramolecular Alder-ene (IMAE) reaction of the derived sulfonamide (±)-12, and the conversion of the ensuing C-3a-arylhexahydroindole (±)-16 into (±)-hamayne via a Pictet-Spengler reaction.",

author = "Laurent Petit and Banwell, \{Martin G.\} and Willis, \{Anthony C.\}",

year = "2011",

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journal = "Organic Letters",

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AU - Petit, Laurent

AU - Banwell, Martin G.

AU - Willis, Anthony C.

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Y1 - 2011/11/4

N2 - The racemic form of the title alkaloid, 1, has been prepared in 13 steps from the ring-fused gem-dibromocyclopropane 7. Key transformations include the thermally induced electrocyclic ring-opening of compound 7, the Pd[0]-catalyzed intramolecular Alder-ene (IMAE) reaction of the derived sulfonamide (±)-12, and the conversion of the ensuing C-3a-arylhexahydroindole (±)-16 into (±)-hamayne via a Pictet-Spengler reaction.

AB - The racemic form of the title alkaloid, 1, has been prepared in 13 steps from the ring-fused gem-dibromocyclopropane 7. Key transformations include the thermally induced electrocyclic ring-opening of compound 7, the Pd[0]-catalyzed intramolecular Alder-ene (IMAE) reaction of the derived sulfonamide (±)-12, and the conversion of the ensuing C-3a-arylhexahydroindole (±)-16 into (±)-hamayne via a Pictet-Spengler reaction.

UR - https://www.scopus.com/pages/publications/80055072241

U2 - 10.1021/ol2023938

DO - 10.1021/ol2023938

M3 - Article

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EP - 5803

JO - Organic Letters

JF - Organic Letters

IS - 21

ER -

The total synthesis of the crinine alkaloid hamayne via a Pd[0]-catalyzed intramolecular Alder-ene reaction

Abstract

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