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

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

Cultural advice

The Australian National University acknowledges, celebrates and pays our respects to the Ngunnawal and Ngambri people of the Canberra region and to all First Nations Australians on whose traditional lands we meet and work, and whose cultures are among the oldest continuing cultures in human history.

Aboriginal and Torres Strait Islander peoples are advised that ANU Library collections may include images, names, voices, and other representations of deceased persons.

Material in the collection may contain terms, language or views that reflect the period in which the item was created and may be considered inappropriate today.

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

Date

2011-11-04

Authors

Petit, Laurent

Banwell, Martin G.

Willis, Anthony C.

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.

URI

https://dspace-test.anu.edu.au/handle/1885/733721764

Collections

DevOps Pure Testing

Source

Organic Letters

Type

Article

DOI

10.1021/ol2023938

Full item page

Cultural advice

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

Date

Authors

Journal Title

Journal ISSN

Volume Title

Publisher

Abstract

Description

Keywords

Citation

URI

Collections

Source

Type

Book Title

Entity type

Access Statement

License Rights

DOI

Restricted until