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Total synthesis and stereochemical revision of relgro and 10'-oxorelgro

Janardhan Gaddam1, G Sudhakar Reddy, Kanakaraju Marumudi

  • 1Department of Organic Synthesis and Process Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad-500007, India. mohapatra@iict.res.in.

Organic & Biomolecular Chemistry
|May 24, 2019
PubMed

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In addition to the oxymercuration–demercuration method, which converts the alkenes to alcohols with Markovnikov orientation, a complementary hydroboration-oxidation method yields the anti-Markovnikov product. The hydroboration reaction, discovered in 1959 by H.C. Brown, involves the addition of a B–H bond of borane to an alkene giving an organoborane intermediate. The oxidation of this intermediate with basic hydrogen peroxide forms an alcohol.
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