Synthetic Efforts toward the Spiroketal Core of Spirangien A
- 8 July 2010
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 75 (15), 5151-5163
- https://doi.org/10.1021/jo100871m
Abstract
Synthetic studies toward the spiroketal core of spirangien A are described. Two synthetic approaches were developed. Both of them use a diastereoselective aldol addition of a lithium enolate derived from a methyl ketone on an aldehyde. In the first approach, the introduction of the (E)-trisubstituted terminal olefin was achieved by using an iron-catalyzed cross-coupling between an alkyl iodide and a vinyl Grignard reagent and a randomly protected spiroketal was obtained. In the second approach, a highly functionalized spiroketal carbamate, which includes 13 stereogenic centers, was successfully isolated.Keywords
This publication has 38 references indexed in Scilit:
- Toward the Total Synthesis of the Brasilinolides: Stereocontrolled Assembly of a C1−C19 Polyol SegmentOrganic Letters, 2008
- Total synthesis of (−)-spirangien A and its methyl esterChemical Communications, 2008
- Synthesis of the C10−C32 Core Structure of Spirangien AOrganic Letters, 2008
- Chemoselective reactions: Toward the synthesis of biologically active natural products with anticancer activitiesPublished by Walter de Gruyter GmbH ,2008
- Synthesis of an Advanced C10–C32 Spiroacetal Fragment and Assignment of the Absolute Configuration of Spirangien AAngewandte Chemie International Edition, 2007
- Desmethylabietospiran, a Naturally Occurring Self-Gelation AgentJournal of Natural Products, 2005
- An NMR Method for Assigning Relative Stereochemistry to β-Hydroxy Ketones Deriving from Aldol Reactions of Methyl KetonesThe Journal of Organic Chemistry, 2002
- Stereochemical control of consecutive stereogenic centres by intramolecular hydroboration of dialkenyl carbinol derivativesJournal of the Chemical Society, Chemical Communications, 1990
- A highly stereocontrolled route to the monensin spiroketal ring systemThe Journal of Organic Chemistry, 1988
- Über Tertiäre Oxoniumsalze, IJournal für Praktische Chemie, 1937