Studies in the total synthesis of himastatin: A revision of the stereochemical assignment Journal Article
| Authors: | Kamenecka, T. M.; Danishefsky, S. J. |
| Article Title: | Studies in the total synthesis of himastatin: A revision of the stereochemical assignment |
| Abstract: | A stereoisomer of the natural product and not himastatin, an unusual dimeric depsipeptide with promising antibiotic and antitumor properties, was obtained from pyrroloindoline anti-cis-1. This result led to a revision of the proposed stereostructure. The new stereostructure was confirmed by the total synthesis, which involves stereoselective access to the pyrroloindoline syn-cis-1 and the 5-hydroxypiperazic acid subunit and features a Stille coupling for the formation of the central carbon-carbon bond. |
| Keywords: | drug structure; drug synthesis; natural product; piperazine derivative; alkaloids; total synthesis; stereochemistry; proton nuclear magnetic resonance; stereoisomerism; carbon; depsipeptide; antibiotics; article; structure elucidation; himastatin |
| Journal Title: | Angewandte Chemie - International Edition |
| Volume: | 37 |
| Issue: | 21 |
| ISSN: | 1433-7851 |
| Publisher: | Wiley Blackwell |
| Date Published: | 1998-11-16 |
| Start Page: | 2993 |
| End Page: | 2995 |
| Language: | English |
| DOI: | 10.1002/(sici)1521-3773(19981116)37:21<2993::aid-anie2993>3.0.co;2-i |
| PROVIDER: | scopus |
| DOI/URL: | |
| Notes: | Article -- Export Date: 12 December 2016 -- Source: Scopus |
