Issue 19, 2013
From the journal:

Chemical Communications

Enantioselective formal synthesis of ent-rhynchophylline and ent-isorhynchophylline†

Mercedes Amat,*a   Carlos Ramos,a   Maria Pérez,a   Elies Molins,b   Pedro Florindo,ac   Maria M. M. Santosc  and  Joan Boscha  

* Corresponding authors

a Laboratory of Organic Chemistry, Faculty of Pharmacy, and Institute of Biomedicine (IBUB), University of Barcelona, 08028-Barcelona, Spain
E-mail: amat@ub.edu
Fax: +34 93 402 45 39
Tel: +34 93 402 45 40

b Institut de Ciència de Materials (CSIC), Campus UAB, 08193-Cerdanyola, Spain

c Faculty of Pharmacy, Research Institute for Medicines and Pharmaceutical Sciences, University of Lisbon, 1649-003 Lisbon, Portugal

Abstract

Starting from (S)-tryptophanol, a formal synthesis of ent-rhynchophylline and ent-isorhynchophylline, involving stereoselective cyclocondensation, spirocyclization, and alkylation reactions, and the final adjustment of the oxidation level at the oxindole and piperidine moieties, is reported.

Graphical abstract: Enantioselective formal synthesis of ent-rhynchophylline and ent-isorhynchophylline

About
Cited by
Related
Download options Please wait...

Supplementary files

Article information

DOI
https://doi.org/10.1039/C2CC38540F
Article type
Communication
Submitted
27 Nov 2012
Accepted
18 Dec 2012
First published
19 Dec 2012

Chem. Commun., 2013,49, 1954-1956

Permissions

Request permissions

Enantioselective formal synthesis of ent-rhynchophylline and ent-isorhynchophylline

M. Amat, C. Ramos, M. Pérez, E. Molins, P. Florindo, M. M. M. Santos and J. Bosch, Chem. Commun., 2013, 49, 1954 DOI: 10.1039/C2CC38540F

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements