469-77-2Relevant academic research and scientific papers
The first enantioselective organocatalytic Mukaiyama-Michael reaction: A direct method for the synthesis of enantioenriched γ-butenolide architecture
Brown, Sean P.,Goodwin, Nicole C.,MacMillan, David W. C.
, p. 1192 - 1194 (2003)
The first enantioselective organocatalytic Mukaiyama-Michael reaction using α,β-unsaturated aldehydes has been accomplished. The use of iminium catalysis has provided a new strategy for the enantioselective addition of 2-silyloxy furans to unsaturated aldehydes to generate a variety of butenolide systems, an important chiral synthon found among many natural isolates. The (2S,5S)-5-benzyl-2-tert-butyl-imidazolidinone amine catalyst has been found to mediate the conjugate addition of a wide variety of substituted and unsubstituted silyloxy furans to unsaturated aldehydes. A diverse range of aldehyde substrates can be accommodated in this new organocatalytic transformation. Application of this new asymmetric technology to the enantioselective total synthesis of spiculisporic acid and the corresponding 5-epi-spiculisporic acid analogue is also discusse. Copyright
Absolute Configuration and Enantioselective Synthesis of Spiculisporic Acid
Brandaenge, Svante,Dahlman, Olof,Lindqvist, Bo,Mahlen, Anders,Moerch, Lars
, p. 837 - 844 (2007/10/02)
The absolute configuration of spiculisporic acid (1), obtained from Penicillium spiculisporum Lehman, has been determined as (3S,4S) by a degradation into (2S,3S)-decylcitric acid (2), a metabolite of a variant of this fungus.The key step in the enantiose
