Total Synthesis of the Marine Alkaloid (±)-Lepadiformine via a Radical Carboazidation
Authors:
- 17 March 2006
- journal article
- letter
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 8 (8) , 1569-1571
Abstract
The total synthesis of lepadiformine has been achieved in 10 steps and 15% overall yield from cyclohexanone. The amino-substituted quaternary carbon center is created through a radical carboazidation reaction. The tricyclic core of lepadiformine is built via an efficient hydrogenation process, involving reduction of the azide and intramolecular reductive amination of a ketone, followed by lactamization of the intermediate γ-aminoester. The hydroxymethyl side chain is introduced according to a modified Takahata procedure after conversion of the lactam into a thiolactam.Keywords
This publication has 23 references indexed in Scilit:
- Tricyclic Marine Alkaloids: Synthetic Approaches to Cylindricines, Lepadiformine, and FasicularinChimia, 2006
- Total Synthesis of Bioactive Tricyclic Marine Alkaloids, Lepadiformine and Related CompoundsBulletin of the Chemical Society of Japan, 2003
- Lepadiformine: A Case Study of the Value of Total Synthesis in Natural Product Structure ElucidationAccounts of Chemical Research, 2002
- Total Synthesis of the Natural Enantiomer of (−)-Lepadiformine and Determination of Its Absolute Stereochemistry This work was supported in part by a Grant for Private Universities provided by the Ministry of Education, Sports, and Culture of Japan and the Promotion and Mutual Aid Corporation for Private Schools of Japan. We are grateful to Professor J. F. Biard for a sample of natural lepadiformine.Angewandte Chemie International Edition, 2002
- Stereoselective Total Syntheses of the Racemic Form and the Natural Enantiomer of the Marine Alkaloid Lepadiformine via a Novel N-Acyliminium Ion/Allylsilane Spirocyclization StrategyThe Journal of Organic Chemistry, 2002
- A New Total Synthesis of the Marine Tunicate Alkaloid LepadiformineOrganic Letters, 2001
- Total Synthesis of (±)-Lepadiformine via an Amidoacrolein CycloadditionOrganic Letters, 2001
- Cardiovascular effects of lepadiformine, an alkaloid isolated from the ascidians Clavelina lepadiformis (Müller) and C. moluccensis (Sluiter)Toxicon, 2001
- First Total Synthesis of the Marine Alkaloids (±)-Fasicularin and (±)-Lepadiformine Based on Stereocontrolled Intramolecular Acylnitroso-Diels−Alder ReactionJournal of the American Chemical Society, 2000
- Lepadiformine, a new marine cytotoxic alkaloid from Clavelina lepadiformis MüllerTetrahedron Letters, 1994