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Total synthesis of the marine alkaloid halitulin |
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| Authors: | Markus R HeinrichWolfgang Steglich Martin G BanwellYoel Kashman |
| Affiliation: | a Department Chemie, Ludwig-Maximilians-Universität München, Butenandtstr. 5-13, D-81377 München, Germany b Research School of Chemistry, Australian National University, Canberra, ACT 0200, Australia c School of Chemistry, Tel Aviv University, Tel Aviv 69978, Israel |
| Abstract: | The structure of the strongly cytotoxic marine alkaloid halitulin (1) has been confirmed by total synthesis and its absolute configuration determined as (15S). The synthesis follows a strategy previously reported by one of us and uses an efficient preparation of the quinoline-7,8-diol unit by modified Baeyer-Villiger and Skraup reactions. The O-benzyl protecting groups were removed in the last step of the synthesis by transfer hydrogenolysis without concomitant reduction of the quinoline ring. The method can be applied for the synthesis of halitulin analogues. |
| Keywords: | natural product synthesis marine metabolites halitulin quinoline-7,8-diols Baeyer-Villiger oxidation Suzuki reaction |
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