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Synthesis of a C1–C9 fragment of rhizoxin

✍ Scribed by Richard J Davenport; Andrew C Regan

Book ID
104210888
Publisher
Elsevier Science
Year
2000
Tongue
French
Weight
91 KB
Volume
41
Category
Article
ISSN
0040-4039

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✦ Synopsis

A C1-C9 fragment of the antitumour macrolide rhizoxin has been synthesised. An Evans' asymmetric aldol reaction was used to set up the first two chiral centres, and an a,b-unsaturated d-lactone was then formed on the acyclic system by an intramolecular Wadsworth-Emmons reaction. Stereoselective hydrogenation was used to set up the cis relative stereochemistry in the saturated d-lactone ring.

📜 SIMILAR VOLUMES

Stereoselective syntheses of the rhizoxi
Stereoselective syntheses of the rhizoxin C(1)C–(9) and C(12)–C(26) subunits
✍ Steven D. Burke; Jian Hong; Andrew P. Mongin 📂 Article 📅 1998 🏛 Elsevier Science 🌐 French ⚖ 324 KB

Stereoselective syntheses of the C(l)-C(9) and C(12)-C(26) subunits of the macrolide antitumor agent rhizoxin are described. Chelation-controlled Ireland-Claisen rearrangement, stereoselective Horner-Wadsworth-Emmons reactions and a thermodynamically-controlled diastereotopic group differentiation a