Enyne metathesis approach towards the cyclopentane motif of jatrophane diterpenes

C. Lentsch; R. Fürst; U. Rinner

doi:10.1055/s-0033-1339923

Enyne metathesis approach towards the cyclopentane motif of jatrophane diterpenes

C. Lentsch, R. Fürst, U. Rinner

University of Vienna

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

Abstract

A short and efficient synthesis of the cyclopentane moiety of the jatrophane diterpene Pl-3 has been developed. The route features an enyne metathesis reaction, and a stereoselective palladium-catalyzed reductive epoxide opening as key steps.

Original language	English
Article number	ST-2013-B0718-L
Pages (from-to)	2665-2670
Number of pages	6
Journal	Synlett
Volume	24
Issue number	20
DOIs	https://doi.org/10.1055/s-0033-1339923
Publication status	Published - 17 Dec 2013
Externally published	Yes

Keywords

metathesis
natural products
palladium
stereoselective synthesis
terpenoids
alcohol
cyclopentane
diterpene
epoxide
euphoheliosnoid D
jatrophane
natural product
pi 3
pubescene D
unclassified drug
article
catalysis
chemical reaction
drug design
drug synthesis
enyne metathesis reaction
stereochemistry
structural homology

Research fields

Metathesis reaction
Terpenes
Euphorbiaceae diterpenes
Stereoselective synthesis

IMC Research Focuses

Materials science

ÖFOS 2012 - Austrian Fields of Study

104008 Catalysis
104015 Organic chemistry
104013 Natural product chemistry

Access to Document

10.1055/s-0033-1339923

Cite this

@article{60a33e883dd54bd8a0764d38ec8b1119,

title = "Enyne metathesis approach towards the cyclopentane motif of jatrophane diterpenes",

abstract = "A short and efficient synthesis of the cyclopentane moiety of the jatrophane diterpene Pl-3 has been developed. The route features an enyne metathesis reaction, and a stereoselective palladium-catalyzed reductive epoxide opening as key steps.",

keywords = "metathesis, natural products, palladium, stereoselective synthesis, terpenoids, alcohol, cyclopentane, diterpene, epoxide, euphoheliosnoid D, jatrophane, natural product, pi 3, pubescene D, unclassified drug, article, catalysis, chemical reaction, drug design, drug synthesis, enyne metathesis reaction, stereochemistry, structural homology",

author = "C. Lentsch and R. F{\"u}rst and U. Rinner",

note = "Export Date: 13 June 2023; Cited By: 6; Correspondence Address: U. Rinner; Institute of Organic Chemistry, University of Vienna, 1090 Vienna, W{\"a}hringer Stra{\ss}e 38, Austria; email: [email protected]; CODEN: SYNLE",

year = "2013",

month = dec,

day = "17",

doi = "10.1055/s-0033-1339923",

language = "English",

volume = "24",

pages = "2665--2670",

journal = "Synlett",

issn = "1437-2096",

number = "20",

}

TY - JOUR

T1 - Enyne metathesis approach towards the cyclopentane motif of jatrophane diterpenes

AU - Lentsch, C.

AU - Fürst, R.

AU - Rinner, U.

N1 - Export Date: 13 June 2023; Cited By: 6; Correspondence Address: U. Rinner; Institute of Organic Chemistry, University of Vienna, 1090 Vienna, Währinger Straße 38, Austria; email: [email protected]; CODEN: SYNLE

PY - 2013/12/17

Y1 - 2013/12/17

N2 - A short and efficient synthesis of the cyclopentane moiety of the jatrophane diterpene Pl-3 has been developed. The route features an enyne metathesis reaction, and a stereoselective palladium-catalyzed reductive epoxide opening as key steps.

AB - A short and efficient synthesis of the cyclopentane moiety of the jatrophane diterpene Pl-3 has been developed. The route features an enyne metathesis reaction, and a stereoselective palladium-catalyzed reductive epoxide opening as key steps.

KW - metathesis

KW - natural products

KW - palladium

KW - stereoselective synthesis

KW - terpenoids

KW - alcohol

KW - cyclopentane

KW - diterpene

KW - epoxide

KW - euphoheliosnoid D

KW - jatrophane

KW - natural product

KW - pi 3

KW - pubescene D

KW - unclassified drug

KW - article

KW - catalysis

KW - chemical reaction

KW - drug design

KW - drug synthesis

KW - enyne metathesis reaction

KW - stereochemistry

KW - structural homology

UR - http://www.scopus.com/inward/record.url?scp=84886169584&partnerID=8YFLogxK

U2 - 10.1055/s-0033-1339923

DO - 10.1055/s-0033-1339923

M3 - Article

SN - 1437-2096

VL - 24

SP - 2665

EP - 2670

JO - Synlett

JF - Synlett

IS - 20

M1 - ST-2013-B0718-L

ER -

Enyne metathesis approach towards the cyclopentane motif of jatrophane diterpenes

Abstract

Keywords

Research fields

IMC Research Focuses

ÖFOS 2012 - Austrian Fields of Study

Access to Document

Other files and links

Fingerprint

Cite this