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Total synthesis of (+)-herbarumin I via intermolecular Nozaki–Hiyama–Kishi reaction

✍ Scribed by Adão Aparecido Sabino; Ronaldo A Pilli

Book ID
104250783
Publisher
Elsevier Science
Year
2002
Tongue
French
Weight
76 KB
Volume
43
Category
Article
ISSN
0040-4039

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✦ Synopsis

The phytotoxin herbarumin I, isolated from Phoma herbarum, was stereoselectively synthesized in 17 steps and 6% yield from L-arabinose featuring the intermolecular Nozaki-Hiyama-Kishi coupling and modified Yamaguchi macrolactonization as key steps.

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Total synthesis of LL-Z1640-2 utilizing
Total synthesis of LL-Z1640-2 utilizing a late-stage intramolecular Nozaki–Hiyama–Kishi reaction
✍ Christopher A. LeClair; Matthew B. Boxer; Craig J. Thomas; David J. Maloney 📂 Article 📅 2010 🏛 Elsevier Science 🌐 French ⚖ 434 KB

A total synthesis of LL-Z1640-2 (2), a potent and selective kinase inhibitor, has been completed. The key step of the convergent synthesis utilized a late-stage intramolecular Nozaki-Hiyama-Kishi (NHK) reaction to close the macrocycle at the C6 0 -C7 0 bond.