1912-35-2Relevant articles and documents
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Porter,Thimann
, p. 229,235 (1965)
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Efficient Synthesis of the Peptide Fragment of the Natural Depsipeptides Jaspamide and Chondramide
Zarezin, Danil P.,Shmatova, Olga I.,Kabylda, Adil M.,Nenajdenko, Valentine G.
, p. 4716 - 4722 (2018/09/10)
A new method for the synthesis of the tripeptide part of the jaspamide and chondramide alkaloids using a Ugi reaction was developed. The reported approach is considerably shorter than all literature syntheses of the peptide parts of these natural products. A family of peptides with different substituents at the 2-position of the indole moiety was prepared to open up access to analogues of these natural products.
Biomimetic total syntheses of borreverine and flinderole alkaloids
Dethe, Dattatraya H.,Erande, Rohan D.,Ranjan, Alok
, p. 10106 - 10120 (2013/11/06)
Dimeric indole alkaloids represent a structurally unique class of natural products having interesting biological activities. Recently, we reported the first total synthesis of flinderoles B and C, structurally unique and potent antimalarial natural products. Central to the design of the approach and by virtue of a one-pot, acid-catalyzed dimerization reaction, the route also provided total synthesis of the borreverine class of natural products. This full account details the progress of efforts that culminated in the protecting-group-free, six-step total synthesis of all of the flindersia alkaloids: dimethylisoborreverine, isoborreverine, flinderoles A-C, and their analogues. A biomimetic approach featuring a scalable and catalytic formal [3 + 2] cycloaddition and Diels-Alder reaction is outlined in detail. On the basis of the experimental observations, a detailed mechanism has been proposed for the dimerization of tertiary alcohol 28.