Revisiting a classic approach to the Aspidosperma alkaloids: An intramolecular Schmidt reaction mediated synthesis of (+)-aspidospermidine

DOI: 10.1021/jo051212n

Source and publish data:

Journal of Organic Chemistry p. 10645 - 10652 (2005)

Update date:2022-08-04

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Authors:

Iyengar, Rajesh

Schildknegt, Klaas

Morton, Martha

Aube, Jeffrey

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Article abstract of DOI:10.1021/jo051212n

A total synthesis of (+)-aspidospermidine (1) is described. The key reactions used in the synthesis of this pentacyclic Aspidosperma alkaloid were a deracemizing imine alkylation/Robinson annulation sequence, a selective "redox ketalization", and an intramolecular Schmidt reaction. A Fischer indolization step carried out on a tricyclic ketone mirrored the sequence reported by Stork and Dolfini in their classic aspidospermine synthesis.

Full text of DOI:10.1021/jo051212n

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