Synthesis of the C3−C19 Segment of Phorboxazole B
- 28 June 2005
- journal article
- research article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 7 (15) , 3255-3258
- https://doi.org/10.1021/ol051039h
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.Keywords
This publication has 19 references indexed in Scilit:
- Axial-Selective Prins Cyclizations by Solvolysis of α-Bromo EthersJournal of the American Chemical Society, 2004
- Total synthesis of (+)-phorboxazole A, a potent cytostatic agent from the sponge Phorbas sp.Organic & Biomolecular Chemistry, 2003
- Simple, Three‐Dimensional Microfabrication of Electrodeposited StructuresAngewandte Chemie International Edition in English, 2003
- A Convergent Total Synthesis of Phorboxazole AAngewandte Chemie International Edition in English, 2003
- Total Synthesis of Phorboxazole AJournal of the American Chemical Society, 1998
- Absolute Configuration of Phorboxazoles A and B from the Marine Sponge Phorbas sp. 1. Macrolide and Hemiketal RingsJournal of the American Chemical Society, 1996
- Phorboxazoles A and B: potent cytostatic macrolides from marine sponge Phorbas speciesJournal of the American Chemical Society, 1995
- Chiral synthesis via organoboranes. 6. Asymmetric allylboration via chiral allyldialkylboranes. Synthesis of homoallylic alcohols with exceptionally high enantiomeric excessThe Journal of Organic Chemistry, 1986
- Direct, regiospecific 2-lithiation of pyridines and pyridine 1-oxides with in situ electrophilic trappingThe Journal of Organic Chemistry, 1983
- Enantioselective synthesis and absolute configuration of (-)-.alpha.-kainic acidJournal of the American Chemical Society, 1982