title: Synthesis of the C3-C19 segment of phorboxazole B.
abstract: [reaction: see text]. Three segment-coupling Prins approaches to the C3-C19 segment of phorboxazole B have been developed. One successful strategy utilized a novel TMSBr-mediated cyclization that proceeded with complete axial selectivity. Displacement of bromide with cesium acetate provided the C13 hydroxyl stereocenter of 22. Additionally, treatment of alpha-acetoxy ether 20 with TFA enabled a more concise synthesis of the C3-C19 target 13 by allowing direct access to the equatorial alcohol.
authors: Department of Chemistry, University of California--Irvine, 92697-2025, USA.
authors: Justin P
authors: JP
authors: Vitale
authors: Scott A
authors: SA
authors: Wolckenhauer
authors: Nga M
authors: NM
authors: Do
authors: Scott D
authors: SD
authors: Rychnovsky
mesh_terms: D000818:Animals; D003500:Cyclization; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010080:Oxazoles / Q000138:chemical synthesis* / Q000737:chemistry; D011161:Porifera / Q000737:chemistry
chemical_list: D006576:Heterocyclic Compounds, 4 or More Rings; D010080:Oxazoles; C408887:phorboxazole A