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Updated: May 22, 2025

Genetic Encoding of a Non-Canonical Amino Acid for the Generation of Antibody-Drug Conjugates Through a Fast Bioorthogonal Reaction
Published on: September 14, 2018
Biomimetic syntheses of kadcoccitane H and kadcotrione C methyl ester
Dattatraya H Dethe1, Salman A Siddiqui1, Chirantan Singha1
1Department of Chemistry, Indian Institute of Technology Kanpur Kanpur - 208016 India ddethe@iitk.ac.in.
Abstract:
Kadcotriones and kadcoccitanes, renowned for their intricate 6/6/5-tricyclic and 6/6/5/6-tetracyclic ring systems, respectively, exhibit promising biological activities. This work proposes a biosynthetic pathway that elucidates how nature synthesizes these triterpenoids from lanosterol. Inspired by this pathway, we present the first biomimetic syntheses of kadcoccitane H and kadcotrione C methyl ester. These syntheses showcase key transformations including olefin transposition, a biomimetic ring contraction/expansion, SeO2 mediated one-pot allylic oxidation/isomerization-elimination/allylic oxidation cascade, regioselective dihydroxylation of sterically hindered double bond, unusual POCl3 mediated cleavage of diol and Still-Gennari olefination.
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Preparation of Amides
The DCC-promoted synthesis of amides begins with the protonation of DCC by carboxylic acid. The protonation makes it a better acceptor. Next, the addition of carboxylate to the protonated carbodiimide gives a reactive acylating agent.
Subsequently, the amine acts as a nucleophile that attacks the acylating agent to form a tetrahedral intermediate. In the...

