The First Total Synthesis of Nakadomarin A
- 29 May 2003
- journal article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 125 (25) , 7484-7485
- https://doi.org/10.1021/ja034464j
Abstract
(-)-Nakadomarin A is a member of manzamine alkaloid isolated from a marine sponge and have a unique hexacyclic structure. The first total synthesis of (+)-nakadomarin A, an enantiomer of natural product, has been accomplished from stereochemically defined 4-oxopiperidin-3-carboxylic acid derivative. The synthesis established the structure of nakadomarin A including absolute configuration.Keywords
This publication has 21 references indexed in Scilit:
- Enantioselective total synthesis of marine alkaloids, manzamine A and related compoundsJournal of Heterocyclic Chemistry, 2000
- Ring Closing Alkyne Metathesis. Comparative Investigation of Two Different Catalyst Systems and Application to the Stereoselective Synthesis of Olfactory Lactones, Azamacrolides, and the Macrocyclic Perimeter of the Marine Alkaloid Nakadomarin AJournal of the American Chemical Society, 1999
- Bioactive products from marine micro- and macro-organismsPublished by Walter de Gruyter GmbH ,1999
- New Approaches to Total Synthesis of Manzamine A, Ircinal A and Related Compounds.Journal of Synthetic Organic Chemistry, Japan, 1999
- The First Total Syntheses of Ircinol A, Ircinal A, and Manzamines A and DJournal of the American Chemical Society, 1998
- An efficient and stereoselective construction of the core structure of the manzamines via an intramolecular Michael reactionTetrahedron Letters, 1998
- Nakadomarin A, a Novel Hexacyclic Manzamine-Related Alkaloid from Amphimedon SpongeThe Journal of Organic Chemistry, 1997
- Ring-Closing Metathesis and Related Processes in Organic SynthesisAccounts of Chemical Research, 1995
- Palladium-Catalyzed Cross-Coupling Reactions of Organoboron CompoundsChemical Reviews, 1995
- The IntramolecularMichael ReactionPublished by Wiley ,1995