Synthesis of (−)-Centrolobine by Prins Cyclizations that Avoid Racemization

Synthesis of (−)-Centrolobine by Prins Cyclizations that Avoid Racemization

The segment-coupling Prins cyclization avoids two of the problems common to other Prins cyclization protocols:  side-chain exchange and partial racemization by reversible 2-oxonia Cope rearrangement. Model studies demonstrate the stereochemical fidelity of Prins cyclizations using α-acetoxy ethers c...

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Veröffentlicht in:Organic letters 2002-10, Vol.4 (22), p.3919-3922
Hauptverfasser: Marumoto, Shinji, Jaber, James J, Vitale, Justin P, Rychnovsky, Scott D
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Sprache:eng
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Anti-Bacterial Agents - chemical synthesis
Cyclization
Indicators and Reagents
Optical Rotation
Pyrans - chemical synthesis
Stereoisomerism
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container_issue 22
container_start_page 3919
container_title Organic letters
container_volume 4
creator Marumoto, Shinji
Jaber, James J
Vitale, Justin P
Rychnovsky, Scott D
description The segment-coupling Prins cyclization avoids two of the problems common to other Prins cyclization protocols:  side-chain exchange and partial racemization by reversible 2-oxonia Cope rearrangement. Model studies demonstrate the stereochemical fidelity of Prins cyclizations using α-acetoxy ethers compared with direct aldehyde−alcohol Prins reactions. Furthermore, we propose a mechanism for the racemization observed in some intermolecular Prins cyclizations. Two straightforward syntheses of optically pure (−)-centrolobine highlight the utility of Prins cyclizations.
doi_str_mv 10.1021/ol026751i
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subjects Anti-Bacterial Agents - chemical synthesis
Cyclization
Indicators and Reagents
Optical Rotation
Pyrans - chemical synthesis
Stereoisomerism
title Synthesis of (−)-Centrolobine by Prins Cyclizations that Avoid Racemization
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