Phorboxazole Synthetic Studies. 1. Construction of a C(3−19) Subtarget Exploiting an Extension of the Petasis−Ferrier Rearrangement

Autor:	John Jin Lim, Smith Ab rd, Patrick R. Verhoest, Kevin P. C. Minbiole
Rok vydání:	1999
Předmět:	Ferrier rearrangement Chemistry Stereochemistry Organic Chemistry Total synthesis Heterocyclic Compounds 4 or More Rings Biochemistry Yield (chemistry) Lewis acids and bases Physical and Theoretical Chemistry Acids Oxazoles Oxidation-Reduction Dimethylaluminum chloride
Zdroj:	Organic Letters. 1:909-912
ISSN:	1523-7052 1523-7060
Popis:	[formula: see text] In this, the first of two letters, we outline our overall strategy for the total synthesis of phorboxazoles A (1) and B (2), rare oxazole-containing macrolides possessing extraordinary antimitotic activity, and describe the assembly of a C(3-19) subtarget (-)-5 for the total synthesis of phorboxazole A. The synthesis of (-)-5 was achieved in 15 linear steps (12% overall yield), exploiting a modification of the Petasis-Ferrier rearrangement to construct the C(11-15) cis-tetrahydropyran. Dimethylaluminum chloride (Me2AlCl) proved to be the Lewis acid of choice for the Petasis-Ferrier rearrangement.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::962ec8aa3fedabbe44d2d0d7d603f608 https://doi.org/10.1021/ol990830l Zobrazit plný text záznamu