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Total Synthesis of (+)‐Sacrolide A
Author(s) -
Thirupathi Barla,
Jena Bighnanshu K.
Publication year - 2019
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201900192
Subject(s) - kinetic resolution , yield (engineering) , hydrolysis , total synthesis , chemistry , alcohol , stereochemistry , combinatorial chemistry , catalysis , enantioselective synthesis , organic chemistry , materials science , metallurgy
Abstract A simple and an efficient synthesis of (+)‐sacrolide A has been achieved from a known compound 10 in 12 steps with 9% overall yield. Key steps involved are Jacobsen's hydrolytic kinetic resolution, Sharpless asymmetric epoxidation, trans ‐selective hydrometallation of the propargylic alcohol, and acid‐catalyzed Kita macrolactonization.