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Application of chiral (E)-crotylsilanes in synthesis: The asymmetric synthesis of the C19C34 spiroketal fragment of rutamycin B

✍ Scribed by Nareshkumar F. Jain; James S. Panek

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

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✦ Synopsis

The asymmetric synthesis of the spiroketal fragment of mtamycin B is reported employing allylsilane bond construction methodology for the introduction of five of the eight stereogenic centers. In this paper, the construction of the CI9-C28 and C29-C34 fragments as well as their coupling through an alkylation reaction of a lithiated N,N-dimethylhydrazone are described.

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Synthesis of the spiroketal segment (C19
Synthesis of the spiroketal segment (C19C34) of the rutamycins, antifungal metabolites of Streptomyces species
✍ James D. White; Yoshihiro Ohba; Warren J. Porter; Shan Wang 📂 Article 📅 1997 🏛 Elsevier Science 🌐 French ⚖ 170 KB

A convergent synthesis of the spiroketal subunit of rutamycins A and B has been devised via Julia coupling of sulfone 14 with aldehyde 23; the pentahydroxy ketone 3 derived from 25 underwent spontaneous cyclization to spiroketal 4.