Five-Step Total Synthesis of (±)-Aspidospermidine by a Lactam Strategy via an Azomethine Ylide

A five-step total synthesis of (±)-aspidospermidine (1) based on a lactam strategy is reported. Our synthesis features an iridium-catalyzed reductive Michael addition/[3+2] cycloaddition cascade to give a tricyclic ketone intermediate from a simple lactam via an azomethine ylide. The developed strategy enables easily available lactams to be used as stable surrogates of multisubstituted amines and would be applicable to a unified total synthesis of complex Aspidosperma alkaloids.

Medienart:

E-Artikel

Erscheinungsjahr:

2021

Erschienen:

2021

Enthalten in:

Zur Gesamtaufnahme - volume:23

Enthalten in:

Organic letters - 23(2021), 8 vom: 16. Apr., Seite 3058-3063

Sprache:

Englisch

Beteiligte Personen:

Katahara, Seiya [VerfasserIn]
Sugiyama, Yasukazu [VerfasserIn]
Yamane, Mina [VerfasserIn]
Komiya, Yukinori [VerfasserIn]
Sato, Takaaki [VerfasserIn]
Chida, Noritaka [VerfasserIn]

Links:

Volltext

Themen:

Journal Article
Research Support, Non-U.S. Gov't

Anmerkungen:

Date Completed 16.06.2021

Date Revised 16.06.2021

published: Print-Electronic

Citation Status PubMed-not-MEDLINE

doi:

10.1021/acs.orglett.1c00735

funding:

Förderinstitution / Projekttitel:

PPN (Katalog-ID):

NLM323779751