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Studies Towards the Stereoselective Total Synthesis of 7‐ O ‐methylnigrosporolide
Author(s) -
Baikadi Karunakar,
Talakokkula Anil,
Narsaiah A. Venkat
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.201900863
Subject(s) - wittig reaction , stereoselectivity , yield (engineering) , total synthesis , chemistry , hydrolysis , stereochemistry , kinetic resolution , reduction (mathematics) , d mannitol , combinatorial chemistry , mannitol , organic chemistry , mathematics , materials science , catalysis , enantioselective synthesis , geometry , metallurgy
The first synthetic approach towards the cytotoxic agent, 7‐ O ‐methylnigrosporolide is described in 13 linear steps with 10.5% overall yield. The synthesis started from commercially available starting materials, D ‐mannitol and 5‐hexenol. The key features of the synthetic pathway involved are Hydrolytic Kinetic Resolution, C2‐Wittig, CBS reduction, Horner‐Wadsworth‐Emmons reaction, Shiina macrolacto‐nization and Lindlar reduction.