Issue 2, 2006

Asymmetric synthesis, stereochemistry and rearrangement reactions of naturally occurring 7′-hydroxylignano-9,9′-lactones

Abstract

The asymmetric synthesis of a series of (7′S,8R,8′R)-7′-hydroxylignano-9,9′-lactones is presented, among them the mammalian lignan (7′S)-hydroxyenterolactone and (7′S)-parabenzlactone, allowing the stereochemistry of natural occurring (–)-parabenzlactone to be re-assigned. A hydroxylactone rearrangement and its possible mechanisms are discussed. Finally a brief survey of the current naming and numbering variants of 7′-hydroxylignano-9,9′-lactones is presented, along with a suggestion for harmonization of the nomenclature.

Graphical abstract: Asymmetric synthesis, stereochemistry and rearrangement reactions of naturally occurring 7′-hydroxylignano-9,9′-lactones

Article information

Article type
Paper
Submitted
20 Sep 2005
Accepted
17 Nov 2005
First published
12 Dec 2005

Org. Biomol. Chem., 2006,4, 331-341

Asymmetric synthesis, stereochemistry and rearrangement reactions of naturally occurring 7′-hydroxylignano-9,9′-lactones

B. Raffaelli, K. Wähälä and T. Hase, Org. Biomol. Chem., 2006, 4, 331 DOI: 10.1039/B513303C

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