A Combined Tamaru Allylation/Olefin Cross-Metathesis Approach for the Total Syntheses of (±)-Paniculidine B, (±)-Paniculidine C, and 2-Methylcarbazole

Yi Lun Tseng; Min Chieh Liang; I. Chia Chen; Yen-Ku Wu

doi:10.1055/s-0036-1591739

A Combined Tamaru Allylation/Olefin Cross-Metathesis Approach for the Total Syntheses of (±)-Paniculidine B, (±)-Paniculidine C, and 2-Methylcarbazole

Yi Lun Tseng
, Min Chieh Liang
, I. Chia Chen
, Yen-Ku Wu^*

^*Corresponding author for this work

Department of Applied Chemistry

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

8 Scopus citations

Abstract

A concise approach to the total syntheses of racemic paniculidines B and C is described. The route features a combined Tamaru allylation/olefin cross-metathesis sequence for the regiocontrolled synthesis of prenylindole intermediates. In addition, we report a transformation of the prenylated indole into 2-methylcarbazole catalyzed by sulfonic acid-functionalized silica gel.

Original language	English
Article number	st-2017-w0744-l
Pages (from-to)	609-612
Number of pages	4
Journal	Synlett
Volume	29
Issue number	5
DOIs	https://doi.org/10.1055/s-0036-1591739
State	Published - 15 Mar 2018

Keywords

Tamaru allylation
alkaloids
carbazoles
cross-metathesis
prenylindoles
total synthesis

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10.1055/s-0036-1591739

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title = "A Combined Tamaru Allylation/Olefin Cross-Metathesis Approach for the Total Syntheses of (±)-Paniculidine B, (±)-Paniculidine C, and 2-Methylcarbazole",

abstract = "A concise approach to the total syntheses of racemic paniculidines B and C is described. The route features a combined Tamaru allylation/olefin cross-metathesis sequence for the regiocontrolled synthesis of prenylindole intermediates. In addition, we report a transformation of the prenylated indole into 2-methylcarbazole catalyzed by sulfonic acid-functionalized silica gel.",

keywords = "Tamaru allylation, alkaloids, carbazoles, cross-metathesis, prenylindoles, total synthesis",

author = "Tseng, \{Yi Lun\} and Liang, \{Min Chieh\} and Chen, \{I. Chia\} and Yen-Ku Wu",

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T1 - A Combined Tamaru Allylation/Olefin Cross-Metathesis Approach for the Total Syntheses of (±)-Paniculidine B, (±)-Paniculidine C, and 2-Methylcarbazole

AU - Tseng, Yi Lun

AU - Liang, Min Chieh

AU - Chen, I. Chia

AU - Wu, Yen-Ku

PY - 2018/3/15

Y1 - 2018/3/15

N2 - A concise approach to the total syntheses of racemic paniculidines B and C is described. The route features a combined Tamaru allylation/olefin cross-metathesis sequence for the regiocontrolled synthesis of prenylindole intermediates. In addition, we report a transformation of the prenylated indole into 2-methylcarbazole catalyzed by sulfonic acid-functionalized silica gel.

AB - A concise approach to the total syntheses of racemic paniculidines B and C is described. The route features a combined Tamaru allylation/olefin cross-metathesis sequence for the regiocontrolled synthesis of prenylindole intermediates. In addition, we report a transformation of the prenylated indole into 2-methylcarbazole catalyzed by sulfonic acid-functionalized silica gel.

KW - Tamaru allylation

KW - alkaloids

KW - carbazoles

KW - cross-metathesis

KW - prenylindoles

KW - total synthesis

UR - https://www.scopus.com/pages/publications/85038875000

U2 - 10.1055/s-0036-1591739

DO - 10.1055/s-0036-1591739

M3 - Article

AN - SCOPUS:85038875000

SN - 0936-5214

VL - 29

SP - 609

EP - 612

JO - Synlett

JF - Synlett

IS - 5

M1 - st-2017-w0744-l

ER -

A Combined Tamaru Allylation/Olefin Cross-Metathesis Approach for the Total Syntheses of (±)-Paniculidine B, (±)-Paniculidine C, and 2-Methylcarbazole

Abstract

Keywords

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