Enantioselective synthesis of the oxadecalin core of phomactin A via a highly stereoselective Diels-Alder reaction Journal Article
| Authors: | Chemler, S. R.; Iserloh, U.; Danishefsky, S. J. |
| Article Title: | Enantioselective synthesis of the oxadecalin core of phomactin A via a highly stereoselective Diels-Alder reaction |
| Abstract: | matrix presented Phomactin A (1) is a selective antagonist of platelet activating factor (PAF). Herein, we report our progress toward the construction of the oxadecalin core of 1. This route is based on the Diels-Alder cycloaddition of an appropriately functionalized vinyl pyran and a complementary dienophile. A model of this reaction involving 2 and maleic anhydride was conducted. Adduct 3 contains the correct stereochemical arrangements between functional groups necessary for gaining access to phomactin A. |
| Keywords: | chemistry; drug antagonism; fused heterocyclic rings; models, chemical; fungus; fungi; synthesis; stereoisomerism; antithrombocytic agent; heterocyclic compounds with 4 or more rings; chemical model; naphthalene derivative; naphthalenes; platelet aggregation inhibitors; article; maleic anhydride; oxadecalin; phomactin a; thrombocyte activating factor; maleic anhydrides; platelet activating factor |
| Journal Title: | Organic Letters |
| Volume: | 3 |
| Issue: | 19 |
| ISSN: | 1523-7060 |
| Publisher: | American Chemical Society |
| Date Published: | 2001-09-20 |
| Start Page: | 2949 |
| End Page: | 2951 |
| Language: | English |
| DOI: | 10.1021/ol0161357 |
| PUBMED: | 11554815 |
| PROVIDER: | scopus |
| DOI/URL: | |
| Notes: | Export Date: 21 May 2015 -- Source: Scopus |
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