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First Stereoselective Synthesis of the Cytotoxic Polyketide (4 R )‐1‐(3,5‐Dihydroxyphenyl)‐4‐hydroxypentan‐2‐one
Author(s) -
Rajendra Prasad Kothakonda,
Purushotham Reddy Sudina,
Suresh Babu Katragadda,
Madhusudana Rao Janaswamy
Publication year - 2015
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.201400158
Subject(s) - chemistry , stereoselectivity , polyketide , stereochemistry , kinetic resolution , cytotoxic t cell , grignard reaction , hydrolysis , alcohol , combinatorial chemistry , enantioselective synthesis , organic chemistry , enzyme , biosynthesis , in vitro , catalysis , biochemistry , reagent
The first stereoselective synthesis of the cytotoxic polyketide (4 R )‐1‐(3,5‐dihydroxyphenyl)‐4‐hydroxypentan‐2‐one ( 1 ) was achieved from readily available propylene oxide and 3,5‐dimethoxybenzyl alcohol. The synthesis involves Jacobsen 's hydrolytic kinetic resolution (HKR) and Grignard reaction as key steps.