Synthesis of Neplanocin A and Its 3′-Epimer via an Intramolecular Baylis–Hillman Reaction
✍ Scribed by Tan, Yun Xuan; Santhanakrishnan, Sridhar; Yang, Hai Yan; Chai, Christina L. L.; Tam, Eric Kwok Wai
- Book ID
- 126057268
- Publisher
- American Chemical Society
- Year
- 2014
- Tongue
- English
- Weight
- 585 KB
- Volume
- 79
- Category
- Article
- ISSN
- 0022-3263
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In this communication we report a stereoselective total synthesis of N-Boc-dolaproine (Dap), an amino acid residue of the antineoplastic pentapeptide Dolastatin 10. Our strategy is based on a Baylis-Hillman reaction between N-Boc-prolinal and methyl acrylate, followed by a diastereoselective double