Synthesis of the spiroketal segment (C19C34) of the rutamycins, antifungal metabolites of Streptomyces species
✍ Scribed by James D. White; Yoshihiro Ohba; Warren J. Porter; Shan Wang
- Publisher
- Elsevier Science
- Year
- 1997
- Tongue
- French
- Weight
- 170 KB
- Volume
- 38
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
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.
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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 a
The CI-C9 segment of epothilons was generated by an aldol reaction between chiral aldehyde 3 and ethyl ketone 4. Removal of the TBS protecting groups and debenzylation generated spiro ketal 13 which was analyzed by X-ray crystallography.