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Stereoselective synthesis of a C1–C6 fragment of pinnatoxin A via a 1,4-addition/alkylation sequence

✍ Scribed by Seiichi Nakamura; Fumiaki Kikuchi; Shunichi Hashimoto

Book ID
108284336
Publisher
Elsevier Science
Year
2008
Tongue
English
Weight
201 KB
Volume
19
Category
Article
ISSN
0957-4166

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Stereoselective synthesis of the C1–C13
Stereoselective synthesis of the C1–C13 fragment of bistramide A
✍ Marie-Aude Hiebel; Béatrice Pelotier; Olivier Piva 📂 Article 📅 2010 🏛 Elsevier Science 🌐 French ⚖ 486 KB

The C1-C13 fragment of bistramide A was prepared from 5-hexenoic acid in 15 linear steps and in 16% overall yield. The core 2,6-trans-tetrahydropyran ring was obtained via a kinetically controlled oxa-Michael cyclization from the corresponding chiral a,b-unsaturated hydroxyester. This precursor was