Synthesis of an Enantiomerically Pure Building Block for the Synthesis of Hydroporphyrins

Adukpo, Genevieve Etornam; Borrmann, Tobias; Manski, René; Díaz, Rosa I. Sáez; Stohrer, Wolf‐Dieter; Montforts, Franz‐Peter

doi:10.1002/ejoc.200600656

Eur J Org Chem

2006

DOI: 10.1002/ejoc.200600656

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Synthesis of an Enantiomerically Pure Building Block for the Synthesis of Hydroporphyrins

Genevieve Etornam Adukpo

Tobias Borrmann

René Manski

et al.

Abstract: The enantiomerically pure pyrrolidine diester 4 is a useful building block for the synthesis of chiral hydroporphyrin compounds. Treatment of optically active aromatic amines with bislactone 5 gave pairs of N-alkylated lactam-lactone diastereomers 6 and 8. These diastereomers were separated by MPL chromatography and in the case of 8 they could be

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Cited by 3 publications

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Lewis Acid Catalyzed Cyclopropane Ring‐Opening‐Cyclization Cascade Using Thioureas as a N,N‐bisnucleophile: Synthesis of Bicyclic Furo‐, Pyrano‐, and Pyrrololactams via a Formal [4+1]‐Addition

Ratzenböck,

Kobras,

Rustler

et al. 2024

Chemistry A European J

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Fused bicyclic cyclopropanes were converted by Lewis acid‐catalysis with thioureas to furo‐, pyrano, and pyrrololactams with yields of up to 99% and high diastereoselectivity. The formation of the title compounds, representing a formal [4+1]‐cycloaddition to a donor‐acceptor substituted cyclopropane, follows a cascade reaction involving SN1‐type ring‐opening addition and cyclization. Thiourea, being a cost‐effective and odorless reagent, acts as an N,N‐bis‐nucleophile to generate bicyclic compounds containing an N‑substituted γ‐lactam moiety.

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Lewis Acid Catalyzed Cyclopropane Ring‐Opening‐Cyclization Cascade Using Thioureas as a N,N‐bisnucleophile: Synthesis of Bicyclic Furo‐, Pyrano‐, and Pyrrololactams via a Formal [4+1]‐Addition

Ratzenböck,

Kobras,

Rustler

et al. 2024

Chemistry A European J

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Synthesis of enantiopure furo[2,3-b]pyrroles

Nair

Ibnusaud

2014

Tetrahedron Letters

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De NovoSynthesis of Gem-Dialkyl Chlorophyll Analogues for Probing and Emulating Our Green World

2015

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Woodward reported his infamous synthesis of chlorin e 6 trimethyl ester, a known synthetic precursor to chlorophyll a. [59][60][61][62][63][64]124 The work was posited on a half-century of intensive studies by many investigators in tetrapyrrole chemistry and began a decade after the close of Fischer's lifetime of research 125−128 (which included an uncompleted synthetic program directed toward chlorophylls 15 ). Indeed, "he read all the umpteen papers on the chlorophylls written by Willstaẗter and Fischer, including the experimental parts." 129 The Woodward synthesis of chlorin e 6 trimethyl ester required 46 steps, of which 24 were spent on converting the sole precursor, Knorr's pyrrole, to the four pyrroles destined to form rings A−D; 7 additional steps accrued to obtain the dipyrromethanes that constitute the Eastern and Western halves (Scheme 13, the step numbers are identical to those shown in ref 64.). The first step formed the Knorr pyrrole (in several kg quantities), the next 24 steps were divided into four parallel paths, whereas the remaining 21 steps proceeded in linear fashion. Remarkable features of the synthesis include the directed intramolecular joining (via an imine) of the Eastern and Western halves (step 33), construction of the acrylate Scheme 10. Hydrogenation of a Porphyrin to Form a Chlorin Scheme 11. Representative meso-Tetraarylchlorins Scheme 12. Methyl Pyropheophorbide a

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Synthesis of an Enantiomerically Pure Building Block for the Synthesis of Hydroporphyrins

Cited by 3 publications

References 29 publications

Lewis Acid Catalyzed Cyclopropane Ring‐Opening‐Cyclization Cascade Using Thioureas as a N,N‐bisnucleophile: Synthesis of Bicyclic Furo‐, Pyrano‐, and Pyrrololactams via a Formal [4+1]‐Addition

Lewis Acid Catalyzed Cyclopropane Ring‐Opening‐Cyclization Cascade Using Thioureas as a N,N‐bisnucleophile: Synthesis of Bicyclic Furo‐, Pyrano‐, and Pyrrololactams via a Formal [4+1]‐Addition

Synthesis of enantiopure furo[2,3-b]pyrroles

De NovoSynthesis of Gem-Dialkyl Chlorophyll Analogues for Probing and Emulating Our Green World

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