Synthesis of the C(1)−C(25) Fragment of Amphidinol 3: Application of the Double-Allylboration Reaction for Synthesis of 1,5-Diols
- 1 March 2005
- journal article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 7 (7) , 1411-1414
- https://doi.org/10.1021/ol050250q
Abstract
[structure: see text] A synthesis of the C(1)-C(25) fragment of amphidinol 3 is described. The synthesis features two applications of double allylboration reaction methodology for the highly stereoselective synthesis of 1,5-diol units in the C(1)-C(15) segment.Keywords
This publication has 24 references indexed in Scilit:
- Synthesis of a C29−C51 Subunit of Spongistatin 1 (Altohyrtin A) Starting from (R)-3-Benzyloxy-2-methylpropan-1-olThe Journal of Organic Chemistry, 2000
- Absolute Configuration of Amphidinol 3, the First Complete Structure Determination from Amphidinol Homologues: Application of a New Configuration Analysis Based on Carbon−Hydrogen Spin-Coupling ConstantsJournal of the American Chemical Society, 1999
- Catalytic Asymmetric DihydroxylationChemical Reviews, 1994
- Substrate-directable chemical reactionsChemical Reviews, 1993
- Palladium-catalyzed inter- and intramolecular cross-coupling reactions of B-alkyl-9-borabicyclo[3.3.1]nonane derivatives with 1-halo-1-alkenes or haloarenes. Syntheses of functionalized alkenes, arenes, and cycloalkenes via a hydroboration-coupling sequenceJournal of the American Chemical Society, 1989
- Enantioselective hydrogenation of allylic and homoallylic alcoholsJournal of the American Chemical Society, 1987
- Directed Homogeneous Hydrogenation [New Synthetic Methods (65)]Angewandte Chemie International Edition in English, 1987
- Readily accessible 12-I-5 oxidant for the conversion of primary and secondary alcohols to aldehydes and ketonesThe Journal of Organic Chemistry, 1983
- Ivermectin, a new broad-spectrum antiparasitic agentJournal of Medicinal Chemistry, 1980
- Sulfur trioxide in the oxidation of alcohols by dimethyl sulfoxideJournal of the American Chemical Society, 1967