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Synthetic studies on maduropeptin chromophore 2. Synthesis of the madurosamine aryl amide and the C1′C9′ fragments

✍ Scribed by K.C. Nicolaou; Kazunori Koide; Jinyou Xu; Mark H. Izraelewicz

Publisher
Elsevier Science
Year
1997
Tongue
French
Weight
179 KB
Volume
38
Category
Article
ISSN
0040-4039

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✦ Synopsis

A retrosynthetic analysis (Scheme 1) of maduropeptin chromophore artifact 1 defined compounds 2 and 3 as required building blocks. The construction of 2 was achieved starting from the 2,5-dimethyl derived aromatic acid 8 and the D-serine derived 6-1actane 12 (Scheme 2), whereas the synthesis of 3 utilized an Evans's aldol condensation reaction between aldehyde 13 and chiral auxiliary 14 (Scheme 3).

📜 SIMILAR VOLUMES

Synthetic studies on maduropeptin chromo
Synthetic studies on maduropeptin chromophore 1. Construction of the aryl ether and attempted synthesis of the [7.3.0] bicyclic system
✍ K.C. Nicolaou; Kazunori Koide 📂 Article 📅 1997 🏛 Elsevier Science 🌐 French ⚖ 220 KB

The aryl ether system of the maduropeptin chromophore artifact I was constructed via an aldol type condensation (7+6, Schemes 1 and 2, 7+19, Scheme 4), but attempted synthesis and ring closure of aldehyde 25 (Scheme 4) to afford the enediyne core of 1 failed.