The Synthesis of Melohenine B and a Related Natural Product

Christopher Stuart Lancefield; Linna Zhou; Tomas Lebl; Alexandra Martha Zoya Slawin; Nicholas James Westwood

doi:10.1021/ol302859j

The Synthesis of Melohenine B and a Related Natural Product

Christopher Stuart Lancefield
, Linna Zhou
, Tomas Lebl
, Alexandra Martha Zoya Slawin
, Nicholas James Westwood

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

Abstract

A concise synthesis of melohenine B and O-ethyl-14-epimelohenine B, from eburnamonine, was achieved via a biomimetic diastereoselective singlet oxygen-mediated oxidative cleavage of the indole C2-C7 bond. These studies enabled the assignment of the absolute configuration of the natural products. In line with a proposed biosynthetic pathway, the resulting nine-membered ring containing products could be converted to the corresponding quinolones.

Original language	English
Pages (from-to)	6166-6169
Number of pages	4
Journal	Organic Letters
Volume	14
Issue number	24
DOIs	https://doi.org/10.1021/ol302859j
Publication status	Published - 21 Dec 2012

Access to Document

10.1021/ol302859j

Handle.net

Persistent link

Using molecular oxygen in synthesis: applications in lignin valorisation and natural product synthesis
Lancefield, C. (Author), Westwood, N. (Supervisor), 24 Jun 2015
Student thesis: Doctoral Thesis (PhD)

Cite this

@article{6c1967db01954e12a0481144101842a5,

title = "The Synthesis of Melohenine B and a Related Natural Product",

abstract = "A concise synthesis of melohenine B and O-ethyl-14-epimelohenine B, from eburnamonine, was achieved via a biomimetic diastereoselective singlet oxygen-mediated oxidative cleavage of the indole C2-C7 bond. These studies enabled the assignment of the absolute configuration of the natural products. In line with a proposed biosynthetic pathway, the resulting nine-membered ring containing products could be converted to the corresponding quinolones.",

author = "Lancefield, \{Christopher Stuart\} and Linna Zhou and Tomas Lebl and Slawin, \{Alexandra Martha Zoya\} and Westwood, \{Nicholas James\}",

year = "2012",

month = dec,

day = "21",

doi = "10.1021/ol302859j",

language = "English",

volume = "14",

pages = "6166--6169",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society (ACS)",

number = "24",

}

TY - JOUR

T1 - The Synthesis of Melohenine B and a Related Natural Product

AU - Lancefield, Christopher Stuart

AU - Zhou, Linna

AU - Lebl, Tomas

AU - Slawin, Alexandra Martha Zoya

AU - Westwood, Nicholas James

PY - 2012/12/21

Y1 - 2012/12/21

N2 - A concise synthesis of melohenine B and O-ethyl-14-epimelohenine B, from eburnamonine, was achieved via a biomimetic diastereoselective singlet oxygen-mediated oxidative cleavage of the indole C2-C7 bond. These studies enabled the assignment of the absolute configuration of the natural products. In line with a proposed biosynthetic pathway, the resulting nine-membered ring containing products could be converted to the corresponding quinolones.

AB - A concise synthesis of melohenine B and O-ethyl-14-epimelohenine B, from eburnamonine, was achieved via a biomimetic diastereoselective singlet oxygen-mediated oxidative cleavage of the indole C2-C7 bond. These studies enabled the assignment of the absolute configuration of the natural products. In line with a proposed biosynthetic pathway, the resulting nine-membered ring containing products could be converted to the corresponding quinolones.

U2 - 10.1021/ol302859j

DO - 10.1021/ol302859j

M3 - Article

SN - 1523-7060

VL - 14

SP - 6166

EP - 6169

JO - Organic Letters

JF - Organic Letters

IS - 24

ER -

The Synthesis of Melohenine B and a Related Natural Product

Abstract

Access to Document

Handle.net

Fingerprint

Student theses

Using molecular oxygen in synthesis: applications in lignin valorisation and natural product synthesis

Cite this