Synthesis of (±)-γ-Lycorane by Using an Intramolecular Friedel-Crafts Reaction

Bao Nguyen Do Doan; Xin Yi Tan; Chin May Ang; Roderick W. Bates

doi:10.1055/s-0036-1589067

Synthesis of (±)-γ-Lycorane by Using an Intramolecular Friedel-Crafts Reaction

Bao Nguyen Do Doan, Xin Yi Tan, Chin May Ang, Roderick W. Bates^*

^*Corresponding author for this work

Nanyang Technological University

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

14 Citations (Scopus)

Abstract

A total synthesis of γ-lycorane has been achieved by employing N -tosylpyrrole as a key building block. The synthesis employs both an intermolecular and an intramolecular Friedel-Crafts reaction, as well as a completely diastereoselective hydrogenation of a late-stage pyrrole intermediate.

Original language	English
Pages (from-to)	4711-4716
Number of pages	6
Journal	Synthesis
Volume	49
Issue number	20
DOIs	https://doi.org/10.1055/s-0036-1589067
Publication status	Published - Oct 17 2017
Externally published	Yes

ASJC Scopus Subject Areas

Catalysis
Organic Chemistry

Keywords

Friedel-Crafts
heterocycle
hydrogenation
pyrrole

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10.1055/s-0036-1589067

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abstract = "A total synthesis of γ-lycorane has been achieved by employing N -tosylpyrrole as a key building block. The synthesis employs both an intermolecular and an intramolecular Friedel-Crafts reaction, as well as a completely diastereoselective hydrogenation of a late-stage pyrrole intermediate.",

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AU - Doan, Bao Nguyen Do

AU - Tan, Xin Yi

AU - Ang, Chin May

AU - Bates, Roderick W.

PY - 2017/10/17

Y1 - 2017/10/17

N2 - A total synthesis of γ-lycorane has been achieved by employing N -tosylpyrrole as a key building block. The synthesis employs both an intermolecular and an intramolecular Friedel-Crafts reaction, as well as a completely diastereoselective hydrogenation of a late-stage pyrrole intermediate.

AB - A total synthesis of γ-lycorane has been achieved by employing N -tosylpyrrole as a key building block. The synthesis employs both an intermolecular and an intramolecular Friedel-Crafts reaction, as well as a completely diastereoselective hydrogenation of a late-stage pyrrole intermediate.

KW - Friedel-Crafts

KW - heterocycle

KW - hydrogenation

KW - pyrrole

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ER -

Synthesis of (±)-γ-Lycorane by Using an Intramolecular Friedel-Crafts Reaction

Abstract

ASJC Scopus Subject Areas

Keywords

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