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Total Synthesis of Cryptorigidifoliol K: Confirmation of Structure and Absolute Configuration
Author(s) -
Sudhakar Reddy G.,
Arjunreddy Mallampudi N.,
Lakshmi Jerripothula K.,
Mohapatra Debendra K.
Publication year - 2018
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201800522
Subject(s) - chemistry , stereocenter , total synthesis , isomerization , stereochemistry , absolute configuration , tandem , natural product , enantioselective synthesis , organic chemistry , catalysis , materials science , composite material
Total synthesis of the revised cryptorigidifoliol K and 2′‐ epi ‐cryptorigidifoliol K was accomplished. Salient features of the synthesis involve tandem isomerization followed by C−O and C−C bond forming reaction, iodolactonization and Nozaki‐Hiyama‐Kishi reaction. The synthesis allowed for confirmation of the structure as well as the elucidation of the unassigned stereocenter present in the side chain of the revised structure by correlating the spectral and analytical data of the synthetic cryptorigidifoliol K and 2′‐ epi ‐cryptorigidifoliol K with the natural product data, which was found to be 1 S ,5 R ,7 S ,2′ R ,3′ E .