GENERAL-APPROACH FOR THE SYNTHESIS OF MACROLINE SARPAGINE ALKALOIDS -THE TOTAL SYNTHESIS OF (+)-MACROLINE/

Authors
BI YZ COOK JM
Citation
Yz. Bi et Jm. Cook, GENERAL-APPROACH FOR THE SYNTHESIS OF MACROLINE SARPAGINE ALKALOIDS -THE TOTAL SYNTHESIS OF (+)-MACROLINE/, Tetrahedron letters, 34(28), 1993, pp. 4501-4504
Citations number
20
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
34
Issue
28
Year of publication
1993
Pages
4501 - 4504
Database
ISI
SICI code
0040-4039(1993)34:28<4501:GFTSOM>2.0.ZU;2-W
Abstract
(+)-Macroline 1 and a more stable equivalent 2 were synthesized from t he tetracyclic ketone 5. The key steps in the synthesis involved a ste reoselective Claisen rearrangement followed by hydroboration-oxidation of the resulting olefin 14 to set the correct stereochemistry at C-15 and C-16.