Eine Entdeckung während der Totalsynthese — Epimerisierung der CP-Verbindungen an C7: Ist (7S)-CP-263,114 ein Fermentationsprodukt?

Eine intramolekulare Diels‐Alder‐Reaktion mit substratvermittelter Kontrolle der Diastereoselektivität war die Grundlage für die asymmetrische Synthese des Grundgerüsts der CP‐Verbindungen 2. Das gezielt entworfene Trien 1 – es enthält eine sperrige chirale Gruppe, die die Seitenselektivität der Cycloaddition beeinflusst – wurde mit 70 % de zum Hauptdiastereomer 2 umgesetzt (siehe Schema). Die Aufklärung der absoluten Konfiguration dieser Vorstufe ermöglichte die enantioselektive Synthese der bioaktiven CP‐Moleküle und eröffnet nun den Zugang zu einfacheren, optisch aktiven Analoga.

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The Absolute Configuration and Asymmetric Total Synthesis of the CP Molecules (CP-263,114 and CP-225,917, Phomoidrides B and A)

Nicolaou

Jung

Yoon

et al. 2000

Angewandte Chemie

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The Absolute Configuration and Asymmetric Total Synthesis of the CP Molecules (CP-263,114 and CP-225,917, Phomoidrides B and A)

Nicolaou

Jung

Yoon

et al. 2000

Angew. Chem. Int. Ed.

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An intramolecular Diels–Alder reaction with substrate‐based control of the diastereoselectivity allowed the asymmetric synthesis of the core of the CP compounds 2. The specially designed triene 1, which contains a bulky chiral moiety capable of influencing the facial selectivity of the cycloaddition, was converted into the major diastereomer 2 with 70 % de (see scheme). The elucidation of the absolute configuration of this precursor allowed for the synthesis of the enantiomerically pure forms of the bioactive CP molecules and now sets the stage for the design of simpler, optically active analogues.

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The Synthesis of CP-263,114 and CP-225,917: Striking Long-Range Stereocontrol in the Fashioning of C7

Tan

2000

Angewandte Chemie

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Eine Entdeckung während der Totalsynthese — Epimerisierung der CP-Verbindungen an C7: Ist (7S)-CP-263,114 ein Fermentationsprodukt?

Cited by 18 publications

References 32 publications

The Absolute Configuration and Asymmetric Total Synthesis of the CP Molecules (CP-263,114 and CP-225,917, Phomoidrides B and A)

The Absolute Configuration and Asymmetric Total Synthesis of the CP Molecules (CP-263,114 and CP-225,917, Phomoidrides B and A)

The Absolute Configuration and Asymmetric Total Synthesis of the CP Molecules (CP-263,114 and CP-225,917, Phomoidrides B and A)

The Synthesis of CP-263,114 and CP-225,917: Striking Long-Range Stereocontrol in the Fashioning of C7

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