Synthesis of the C(11)-C(20) Segment of the Cytotoxic Macrolide Epothilone B. -The fragment (VIII) is synthesized from (S)-malic acid (I) via 2 Wittig reactions and a Sharpless asymmetric epoxidation. -
Synthesis of the C(11)–C(20) segment of the cytotoxic macrolide epothiline B
✍ Scribed by Johann Mulzer; Andreas Mantoulidis; Elisabeth Öhler
- Publisher
- Elsevier Science
- Year
- 1997
- Tongue
- French
- Weight
- 185 KB
- Volume
- 38
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
Compound 11, representing the C(I 1)-C(20) segment of the macrolide epothilone B (lb) has been prepared using two Wittig reactions and a Sharpless asymmetric epoxidation as the key steps.
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The C( 1)-C(9) segment 3 of the macrolides epothilon A and B 1, two new cytotoxic natural products, has been synthesized in a direct manner. Key steps in the synthesis are a stereoselective aldol reaction of 6 and 7 and a Brown allylation of 9.
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