160238-45-9Relevant articles and documents
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.
Concise diastereoselective synthesis of calcaripeptide C via asymmetric transfer hydrogenation/Pd-induced chiral allenylzinc as a key reaction
Kumaraswamy, Gullapalli,Narayanarao, Vykunthapu,Raju, Ragam
supporting information, p. 8487 - 8494 (2015/08/06)
Synthesis of the natural product calcaripeptide C derived from the fungal metabolite mycelium KF525 of Calcarisporium sp. has been achieved. This complementary approach avoids the use of a stoichiometric amount of chiral auxiliary reagents as commonly used to generate enantioenriched advanced precursors. The enantioselective synthesis of calcaripeptide C is remarkable in that using catalytic reactions sets the two stereogenic centers efficiently with good levels of enantioselectivity. Further diversification of the calcaripeptide C structures is possible by employing a complementary catalytic enantioenriched Ru-catalyst.
Prediction and determination of the stereochemistry of the 1,3,5-trimethyl-substituted alkyl chain in verucopeptin, a microbial metabolite
Yoshimura, Aya,Kishimoto, Shinji,Nishimura, Shinichi,Otsuka, Saori,Sakai, Yuki,Hattori, Akira,Kakeya, Hideaki
, p. 6858 - 6867 (2014/08/18)
For the prediction of the relative stereochemistry of 1,3-dimethyl substitution in alkyl chains, a simple approach based on 1H NMR data was recently proposed; Δδ values of methylene protons located between methyl-substituted methine carbons can