460997-47-1Relevant academic research and scientific papers
Nhatrangin A: Total Syntheses of the Proposed Structure and Six of Its Diastereoisomers
Dias, Luiz C.,Polo, Ellen C.
, p. 4072 - 4112 (2017/04/28)
A total synthesis of the proposed structure of nhatrangin A is described. This strategy relies on two aldol reactions to install the chiral centers at C3/C4 and C3′/C4′, a lithium-mediated coupling between an advanced intermediate alkyne and a Weinreb amide to complete the C1-C13 alkyl scaffold, and a Yamaguchi esterification to set the side chain. Discrepancies in the spectroscopic data between synthetic and natural nhatrangins led us to synthesize six more diastereoisomers of the proposed structure of nhatrangin A.
Polyketide synthesis using the boron-mediated, anti-aldol reactions of lactate-derived ketones: Total synthesis of (-)-ACRL toxin IIIB
Paterson, Ian,Wallace, Debra J.,Cowden, Cameron J.
, p. 639 - 652 (2007/10/03)
The boron-mediated, anti-selective, aldol reactions of ketone 2 (and related derivatives) proceed with high levels of asymmetric induction, diastereoselectivities of up to 200:1 in favour of the aldol adducts 4 are obtained with achiral aldehydes and reag
Studies in polypropionate synthesis: High π-face selectivity in Syn and Anti aldol reactions of chiral boron enolates of lactate-derived ketones
Paterson, Ian,Wallace, Debra J.,Velazquez, Silvia M.
, p. 9083 - 9086 (2007/10/02)
Use of (c)Hex2Bcl/Me2NEt in the aldol reactions of the α'-benzoyloxy ketone 7 with aldehydes leads to high stereoselectivity (97-95.5% ds) for the crystalline anti adducts 11. Under similar conditions, the corresponding benzyl ether 6 favours formation of the syn adducts 9.
