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Issue 2, 2006
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Asymmetric synthesis, stereochemistry and rearrangement reactions of naturally occurring 7′-hydroxylignano-9,9′-lactones

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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

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Article information


Submitted
20 Sep 2005
Accepted
17 Nov 2005
First published
12 Dec 2005

Org. Biomol. Chem., 2006,4, 331-341
Article type
Paper

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

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