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- W2067071751 abstract "A total synthesis of (-)-hemiasterlin has been accomplished in nine steps from 25(8) (>35% yield overall). An improved enantiocontrolled route to the tetramethyltryptophan subunit 32 was developed using an asymmetric Strecker synthesis (five steps, 50% yield from 25), and the dipeptide 22 was prepared in seven steps, 37% yield from valinol. The synthesis exploits the high reactivity of a Bts-protected amino acid chloride in the difficult peptide coupling of sterically hindered amino acid residues 18 and 20 to form 21 (70%, recrystallized) and also uses N-Bts intermediates for the high-yielding N-methylations of 14 and 31. In addition, the Bts-protected di-tert-butyl N-acylimidodicarbonate 33 is shown to undergo efficient coupling with 22 to form 34 (97% in the coupling step; 79% over the activation; coupling sequence from 32)." @default.
- W2067071751 created "2016-06-24" @default.
- W2067071751 creator A5081971106 @default.
- W2067071751 creator A5090482927 @default.
- W2067071751 date "2001-09-28" @default.
- W2067071751 modified "2023-10-03" @default.
- W2067071751 title "A Total Synthesis of (−)-Hemiasterlin Using <i>N</i>-Bts Methodology" @default.
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- W2067071751 doi "https://doi.org/10.1021/jo0104882" @default.
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