Solid-phase total synthesis of the pentacyclic system lamellarins U and L

Pablo Cironi; Ignacio Manzanares; Fernando Albericio; Mercedes Alvarez

doi:10.1021/ol0351192

Solid-phase total synthesis of the pentacyclic system lamellarins U and L

Org Lett. 2003 Aug 7;5(16):2959-62. doi: 10.1021/ol0351192.

Authors

Pablo Cironi¹, Ignacio Manzanares, Fernando Albericio, Mercedes Alvarez

Affiliation

¹ Laboratory of Organic Chemistry, Faculty of Pharmacy, University of Barcelona, 08028 Barcelona, Spain.

PMID: 12889918
DOI: 10.1021/ol0351192

Abstract

[reaction: see text] A total solid-phase synthesis of lamellarins U and L has been achieved. The conversion of an aldehyde group into a formate by a Baeyer-Villiger reaction and a intramolecular [3 + 2] cycloaddition of a 3,4-dihydroisoquinolinium salt over a triple bond comprise the key steps of the process. Each transformation has been controlled with the proper spectroscopic and analytical methods.