Studies in the total synthesis of heliquinomycinone: Proof of concept and assembly of a fully mature spirocyclization precursor Journal Article
| Authors: | Qin, D.; Ren, R. X.; Siu, T.; Zheng, C.; Danishefsky, S. J. |
| Article Title: | Studies in the total synthesis of heliquinomycinone: Proof of concept and assembly of a fully mature spirocyclization precursor |
| Abstract: | A strategy for the synthesis of heliquinomycin, a selective helicase inhibitor, hinges on the spirocyclization of precursor 3. Naphthofuran 1 and aldehyde 2 were readily prepared and used in the synthesis of 3. The key steps in the total synthesis of heliquinomycinone (4) include the regioselective dihydroxylation of 3, and a novel spirocyclization under Mitsunobu conditions. |
| Keywords: | antibiotic agent; unclassified drug; antineoplastic agent; enzyme inhibition; drug structure; drug synthesis; drug mechanism; quinones; crystal structure; cyclization; drug isolation; total synthesis; synthesis (chemical); antitumor agents; furan derivative; spiro compounds; aldehyde; phenol; dihydroxylation; aromatic compounds; article; boron derivative; mitsunobu conditions; griseorhodin; heliquinomycinone; isocoumarin derivative; purpuromycin |
| Journal Title: | Angewandte Chemie - International Edition |
| Volume: | 40 |
| Issue: | 24 |
| ISSN: | 1433-7851 |
| Publisher: | Wiley Blackwell |
| Date Published: | 2001-12-17 |
| Start Page: | 4709 |
| End Page: | 4713 |
| Language: | English |
| DOI: | 10.1002/1521-3773(20011217)40:24<4709::aid-anie4709>3.0.co;2-q |
| PROVIDER: | scopus |
| PUBMED: | 12404391 |
| DOI/URL: | |
| Notes: | Export Date: 21 May 2015 -- Source: Scopus |
