Catalysis in the Total Synthesis of Bryostatin 16
✍ Scribed by Aubry K. Miller
- Publisher
- John Wiley and Sons
- Year
- 2009
- Tongue
- English
- Weight
- 273 KB
- Volume
- 48
- Category
- Article
- ISSN
- 0044-8249
No coin nor oath required. For personal study only.
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Scheme 1. Retrosynthetic analysis of latrunculin B. Scheme 2. Synthesis of two building blocks by iron-catalyzed crosscoupling reactions: a) KHMDS, PhN(Tf) 2 , THF, À 78 8C, 61 %; b) [Fe(acac) 3 ] (10 mol %), THF, À 30 8C, 97 %; c) aqueous NaOH, MeOH, 92 %; d) CDI, THF, 71 %; e) NaH, PMBBr, THF, 77
The bryostatins are a unique family of cancer chemotherapeutic candidates isolated from marine bryozoa. While their molecular mode of action is not known, these macrolactones exhibit high affinities for protein kinase C (PKC) isozymes, compete for the phorbol ester binding site on PKC, and stimulate