One-pot total syntheses of natural products containing a THP-ring backbone: (±)-centrolobine and (±)-civet cat secretion

Hai Zhou; Teck Peng Loh

doi:10.1016/j.tetlet.2009.05.053

One-pot total syntheses of natural products containing a THP-ring backbone: (±)-centrolobine and (±)-civet cat secretion

Hai Zhou, Teck Peng Loh^*

^*Corresponding author for this work

Nanyang Technological University

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

30 Citations (Scopus)

Abstract

A one-pot strategy is devised and applied to the total syntheses of natural products with a THP-ring backbone. A special feature of this one-pot synthesis is the recyclability of the indium complex byproduct generated from the indium-mediated allylation reaction for concurrent catalysis in subsequent steps. Centrolobine and civet cat secretion are synthesized via this new method in overall yields of 58% and 23%, respectively.

Original language	English
Pages (from-to)	4368-4371
Number of pages	4
Journal	Tetrahedron Letters
Volume	50
Issue number	30
DOIs	https://doi.org/10.1016/j.tetlet.2009.05.053
Publication status	Published - Jul 29 2009
Externally published	Yes

ASJC Scopus Subject Areas

Biochemistry
Drug Discovery
Organic Chemistry

Keywords

Centrolobine
Civet cat secretion
Natural product
One-pot
THP
Total synthesis

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10.1016/j.tetlet.2009.05.053

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T2 - (±)-centrolobine and (±)-civet cat secretion

AU - Zhou, Hai

AU - Loh, Teck Peng

PY - 2009/7/29

Y1 - 2009/7/29

N2 - A one-pot strategy is devised and applied to the total syntheses of natural products with a THP-ring backbone. A special feature of this one-pot synthesis is the recyclability of the indium complex byproduct generated from the indium-mediated allylation reaction for concurrent catalysis in subsequent steps. Centrolobine and civet cat secretion are synthesized via this new method in overall yields of 58% and 23%, respectively.

AB - A one-pot strategy is devised and applied to the total syntheses of natural products with a THP-ring backbone. A special feature of this one-pot synthesis is the recyclability of the indium complex byproduct generated from the indium-mediated allylation reaction for concurrent catalysis in subsequent steps. Centrolobine and civet cat secretion are synthesized via this new method in overall yields of 58% and 23%, respectively.

KW - Centrolobine

KW - Civet cat secretion

KW - Natural product

KW - One-pot

KW - THP

KW - Total synthesis

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EP - 4371

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 30

ER -

One-pot total syntheses of natural products containing a THP-ring backbone: (±)-centrolobine and (±)-civet cat secretion

Abstract

ASJC Scopus Subject Areas

Keywords

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