Total Synthesis of an Anticancer Natural Product (±)-Peharmaline A and Its Analogues

Akshay S. Kulkarni; Rahul D. Shingare; Rambabu Dandela; D. Srinivasa Reddy

doi:10.1002/ejoc.201800949

Total Synthesis of an Anticancer Natural Product (±)-Peharmaline A and Its Analogues

Akshay S. Kulkarni, Rahul D. Shingare, Rambabu Dandela, D. Srinivasa Reddy

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

9 Scopus citations

Abstract

First total synthesis of a rare β-carboline–vasicinone hybrid alkaloid (±)-peharmaline A has been accomplished in just 3 steps starting from known compounds. Stereoselective Pictet–Spengler reaction to nitrogenated tertiary carbon center and one-pot construction of the tricyclic skeleton of vasicinone are the highlights of present synthesis. We have also synthesized structurally close analogues of the natural product by following the developed route.

Original language	English
Pages (from-to)	6453-6456
Number of pages	4
Journal	European Journal of Organic Chemistry
Volume	2018
Issue number	46
DOIs	https://doi.org/10.1002/ejoc.201800949
State	Published - 13 Dec 2018
Externally published	Yes

Keywords

Alkaloids
Cytotoxicity
Natural products
Nitrogen heterocyles
Total synthesis

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Organic Chemistry

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1002/ejoc.201800949

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abstract = "First total synthesis of a rare β-carboline–vasicinone hybrid alkaloid (±)-peharmaline A has been accomplished in just 3 steps starting from known compounds. Stereoselective Pictet–Spengler reaction to nitrogenated tertiary carbon center and one-pot construction of the tricyclic skeleton of vasicinone are the highlights of present synthesis. We have also synthesized structurally close analogues of the natural product by following the developed route.",

keywords = "Alkaloids, Cytotoxicity, Natural products, Nitrogen heterocyles, Total synthesis",

author = "Kulkarni, {Akshay S.} and Shingare, {Rahul D.} and Rambabu Dandela and Reddy, {D. Srinivasa}",

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T1 - Total Synthesis of an Anticancer Natural Product (±)-Peharmaline A and Its Analogues

AU - Kulkarni, Akshay S.

AU - Shingare, Rahul D.

AU - Dandela, Rambabu

AU - Reddy, D. Srinivasa

PY - 2018/12/13

Y1 - 2018/12/13

N2 - First total synthesis of a rare β-carboline–vasicinone hybrid alkaloid (±)-peharmaline A has been accomplished in just 3 steps starting from known compounds. Stereoselective Pictet–Spengler reaction to nitrogenated tertiary carbon center and one-pot construction of the tricyclic skeleton of vasicinone are the highlights of present synthesis. We have also synthesized structurally close analogues of the natural product by following the developed route.

AB - First total synthesis of a rare β-carboline–vasicinone hybrid alkaloid (±)-peharmaline A has been accomplished in just 3 steps starting from known compounds. Stereoselective Pictet–Spengler reaction to nitrogenated tertiary carbon center and one-pot construction of the tricyclic skeleton of vasicinone are the highlights of present synthesis. We have also synthesized structurally close analogues of the natural product by following the developed route.

KW - Alkaloids

KW - Cytotoxicity

KW - Natural products

KW - Nitrogen heterocyles

KW - Total synthesis

UR - http://www.scopus.com/inward/record.url?scp=85055921462&partnerID=8YFLogxK

U2 - 10.1002/ejoc.201800949

DO - 10.1002/ejoc.201800949

M3 - Article

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VL - 2018

SP - 6453

EP - 6456

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 46

ER -

Total Synthesis of an Anticancer Natural Product (±)-Peharmaline A and Its Analogues

Abstract

Keywords

ASJC Scopus subject areas

UN SDGs

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