Evaluation of diene hierarchies for Diels-Alder reactions en route to xestocyclamine A: Elaboration of an ansa bridge by B-alkyl Suzuki macrocyclization Journal Article
| Authors: | Gagnon, A.; Danishefsky, S. J. |
| Article Title: | Evaluation of diene hierarchies for Diels-Alder reactions en route to xestocyclamine A: Elaboration of an ansa bridge by B-alkyl Suzuki macrocyclization |
| Abstract: | A double Michael addition of amine 2 to 1 was a key reaction in the synthesis of the isoquinuclidine core 4 of xestocyclamine A, a protein kinase C inhibitor. The first ansa bridge was formed efficiently by a B-alkyl Suzuki coupling in 3. TBDPS = tert-butyldiphenylsilyl; Ts = p-toluenesulfonyl. |
| Keywords: | unclassified drug; proteins; amines; chemical structure; cyclization; alkaloids; heterocyclic compound; reaction analysis; synthesis; synthesis (chemical); macrocycles; cycloaddition; alkadiene; alkaloid; cross-coupling; annulation; aromatic compounds; article; macrocyclization; xestocyclamine |
| Journal Title: | Angewandte Chemie - International Edition |
| Volume: | 41 |
| Issue: | 9 |
| ISSN: | 1433-7851 |
| Publisher: | Wiley Blackwell |
| Date Published: | 2002-05-03 |
| Start Page: | 1581 |
| End Page: | 1584 |
| Language: | English |
| DOI: | 10.1002/1521-3773(20020503)41:9<1581::aid-anie1581>3.0.co;2-f |
| PROVIDER: | scopus |
| PUBMED: | 19750672 |
| DOI/URL: | |
| Notes: | Corrigendum issued, see DOI: 10.1002/1521-3773(20020902)41:17<3085::AID-ANIE3085>3.0.CO;2-4 -- Export Date: 14 November 2014 -- Source: Scopus |
