77192-46-2Relevant academic research and scientific papers
A short access to 3-hydroxy-4-hydroxymethyltetrahydrofurans: Application to the total synthesis of amphiasterin B4
Salim, Hani,Piva, Olivier
supporting information; experimental part, p. 2257 - 2260 (2009/08/07)
The first total synthesis of amphiasterin B4, a secondary metabolite previously isolated from Plakortis quasiamphiaster has been achieved. The core structure has been reached according to a highly stereoselective one-pot epoxidation/cyclization of an unsa
Chemoenzymatic Preparation of Asymmetrized Tris(hydroxymethyl)methane (THYM*) and of Asymmetrized Bis(hydroxymethyl)acetaldehyde (BHYMA*) as New Highly Versatile Chiral Building Blocks
Guanti, Giuseppe,Banfi, Luca,Narisano, Enrica
, p. 1540 - 1554 (2007/10/02)
A series of asymmetrized tris(hydroxymethyl)methanes 2 and bis(hydroxymethyl)acetaldehydes 3 have been prepared in both enantiomeric forms through a chemoenzymatic methodology.The key step is the highly enantioselective PPL-catalyzed monohydrolysis of 2(E)-alkenyl-1,3-diacetoxypropanes 25-27.A careful study on the effect of unsaturations adjacent to the prochiral center in a series of 2-substituted 1,3-diacetoxypropanes has confirmed the suggested beneficial effect of a ? system in that position but has also unveiled an unprecedented dramatic effect of double-bond configuration on enantioselectivity.A new empirical model for the interpretation of these and other results, based both on polarity and steric arguments, is proposed.This study provides a general protocol for the efficient synthesis of asymmetrized 1,3-propanediols bearing in position 2 saturated or unsaturated carbon chains.
Enzymes in Organic Synthesis: Remarkable Influence of a ? System on the Enantioselectivity in PPL Catalysed Monohydrolysis of 2-Substituted 1,3-Diacetoxypropanes.
Guanti, Giuseppe,Banfi, Luca,Narisano, Enrica
, p. 721 - 724 (2007/10/02)
The results of PPL catalysed monohydrolysis of a series of 2-substituted-1,3-diacetoxypropanes showed that alkinyl and (E) alkenyl substituents led to improvement of yield and enantioselectivity, compared to their saturated analogues.On the contrary, (Z) alkenyl substituents provoked a net reversal of asymmetric induction.
Preparation of Lactones via Tricarbonyliron-Lactone Complexes
Annis, Gary D.,Ley, Steven V.,Self, Christopher R.,Sivaramakrishnan, Ramamoorthy
, p. 270 - 277 (2007/10/02)
A number of tricarbonyliron-lactone complexes have been prepared from vinyl oxirans by treatment with pentacarbonyliron.In certain cases two ν3-allyl complexes were isolated from a single vinyl oxiran.Oxidation of the complexes by cerium (IV) ammonium nitrate in acetonitrile leads predominantly to β-lactones.The stereochemical integrity of the initial complexes is reflected in the formation of the oxidation products.Reduction of these products with lithium aluminium hydride gave the expected diols.
