Spongistatin synthetic studies. 2. Assembly of the C(18–28) spiroketal
✍ Scribed by Amos B. Smith III; Linghang Zhuang; Christopher S. Brook; Qiyan Lin; William H. Moser; Robert E. Lee Trout; Armen M. Boldi
- Publisher
- Elsevier Science
- Year
- 1997
- Tongue
- French
- Weight
- 229 KB
- Volume
- 38
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
The C(18-28) CD-ring spiroketal subunit of the spongistatins, marine polyether macrolides with unprecedented antitumor activity, has been generated via a highly convergent and completely stereocontrolled sequence. Key operations include a one-flask dithiane bisalkylation and a metal-assisted spiroketal equilibration.
📜 SIMILAR VOLUMES
A convergent synthesis of the C(1-17) AB-ring subunit of the spongistatins, exceedingly scarce and highly ant]mitotic polyether macrolides, has been achieved via a one-flask dithiane bisalkylation, stereocontrolled spiroketalization, and Julia sulfone coupling/methylenation. © ]997 Elsevier Science
The C15-C28 portion of altohyrtins (spongistatins) was prepared in a convergent manner from methyl (S)-3hydroxy-2-methylpropionate, D-arabitol, and diacetone-D-glucose via dithiane couplings with epoxides as the key segment coupling process.