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Synthesis of the C(1)-C(9) segment of the cytotoxic macrolides epothilon A and B

✍ Scribed by Johann Mulzer; Andreas Mantoulidis

Publisher
Elsevier Science
Year
1996
Tongue
French
Weight
213 KB
Volume
37
Category
Article
ISSN
0040-4039

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✦ Synopsis

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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Synthesis of the C1ξ—ΈC9 segment of epothi
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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.

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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.