Phorboxazole Synthetic Studies. 2. Construction of a C(20−28) Subtarget, a Further Extension of the Petasis−Ferrier Rearrangement

Autor:	Kevin P. C. Minbiole, Amos B. Smith, Thomas J. Beauchamp, Patrick R. Verhoest
Rok vydání:	1999
Předmět:	Ferrier rearrangement Magnetic Resonance Spectroscopy Stereochemistry Organic Chemistry Total synthesis Heterocyclic Compounds 4 or More Rings Biochemistry Enol chemistry.chemical_compound chemistry Yield (chemistry) Physical and Theoretical Chemistry Oxazoles Oxidation-Reduction
Zdroj:	Organic Letters. 1:913-916
ISSN:	1523-7052 1523-7060
Popis:	[formula: see text] In this, the second of two Letters, we describe the efficient assembly of (+)-4, a C(20-28) subtarget for the total synthesis of phorboxazoles A (1) and B (2). The synthesis was achieved in 12 linear steps (20% overall yield) via Petasis-Ferrier rearrangement of an E/Z mixture of trisubstituted enol ethers (15) to assemble the C(22-26) cis-tetrahydropyran. A mechanism for the observed diastereoconvergence of 15 is proposed. In addition, a new tactic for the synthesis of enol ethers (e.g., 15) based on the elegant work of Julia is described.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::814ebe16c4d3a5f156cdfe8f88ceba8b https://doi.org/10.1021/ol990829m Zobrazit plný text záznamu