Practical total synthesis of 11-deoxydaunomycinone and the first total synthesis of 11-deoxydaunomycin
✍ Scribed by Yasumitsu Tamura; Shuji Akai; Hisakazu Kishimoto; Masayuki Kirihara; Manabu Sasho; Yasuyuki Kita
- Publisher
- Elsevier Science
- Year
- 1987
- Tongue
- French
- Weight
- 288 KB
- Volume
- 28
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
The first total synthesis of the naturally derived second generation anthracycline, ll-deoxydaunomycin (2) is described. Key steps in the synthesis of 1 include an efficient construction of cc-hydroxy methyl ketone moiety at Cg-position, a highly stereoselective synthesis of c>-C7,9-diol, and the first successful use of Cl3-acetal derivative for the qlycosidation.
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## Abstract A simple and highly efficient stereoselective total synthesis of (11__β__)‐11‐methoxycurvularin (**5**), a polyketide natural product, was achieved. The synthesis commenced with a Cu‐mediated regioselective opening of (2__S__)‐2‐methyloxirane (**6**) and comprised a __Keck__ asymmetric
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