Abstract
Synthesis of dolaphenine (2), the thiazole-containing unit of the strongly antineoplastic peptide dolastatin 10 (1), has been summarized. While conversion (4→7 or 4→11) of phenylalanine to thiazolidines (7) or thiazolines (11) was routinely uneventful, a dependable procedure for dehydrogenation of these intermediates to dolaphenine (2, Doe) proved elusive. While several types of specially prepared manganese dioxide were found most effective for the dehydrogenation, yields of dolaphenine varied from almost nil to over 70%. Some of these reactions resulted in partial to complete racemization of the phenylalanine derived chiral carbon.
Original language | English (US) |
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Pages (from-to) | 81-100 |
Number of pages | 20 |
Journal | Heterocycles |
Volume | 39 |
Issue number | 1 |
DOIs | |
State | Published - Dec 31 1994 |
ASJC Scopus subject areas
- Analytical Chemistry
- Pharmacology
- Organic Chemistry