A Conia-Ene-Type Cyclization under Basic Conditions Enables an Efficient Synthesis of (−)-Lycoposerramine R

Felix W.W. Hartrampf; Takayuki Furukawa; Dirk Trauner

doi:10.1002/anie.201610021

A Conia-Ene-Type Cyclization under Basic Conditions Enables an Efficient Synthesis of (−)-Lycoposerramine R

Felix W.W. Hartrampf, Takayuki Furukawa, Dirk Trauner

Chemistry

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

Abstract

An enantioselective total synthesis of the Lycopodium alkaloid lycoposerramine R is presented. It relies on a base-mediated cyclization that resembles the Conia-ene reaction of ynones and gold-catalyzed variants thereof. Thus, hydrindanones and other functionalized ring systems bearing an exocyclic alkene can be rapidly accessed at room temperature without noble metal catalysis or substrate preactivation.

Original language	English (US)
Pages (from-to)	893-896
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	56
Issue number	3
DOIs	https://doi.org/10.1002/anie.201610021
State	Published - Jan 16 2017

Keywords

Conia-ene reaction
alkynes
hydrindanes
lycopodium alkaloids
total synthesis

ASJC Scopus subject areas

Catalysis
General Chemistry

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10.1002/anie.201610021

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AU - Trauner, Dirk

PY - 2017/1/16

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AB - An enantioselective total synthesis of the Lycopodium alkaloid lycoposerramine R is presented. It relies on a base-mediated cyclization that resembles the Conia-ene reaction of ynones and gold-catalyzed variants thereof. Thus, hydrindanones and other functionalized ring systems bearing an exocyclic alkene can be rapidly accessed at room temperature without noble metal catalysis or substrate preactivation.

KW - Conia-ene reaction

KW - alkynes

KW - hydrindanes

KW - lycopodium alkaloids

KW - total synthesis

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A Conia-Ene-Type Cyclization under Basic Conditions Enables an Efficient Synthesis of (−)-Lycoposerramine R

Abstract

Keywords

ASJC Scopus subject areas

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