Premium
Sequential Enyne‐Metathesis/Diels–Alder Strategy: Rapid Access to Sugar–Oxasteroid–Quinone Hybrids
Author(s) -
Sayyad Ashik A.,
Kaliappan Krishna P.
Publication year - 2017
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201700599
Subject(s) - quinone , chemistry , enyne metathesis , sugar , enyne , metathesis , diels–alder reaction , organic chemistry , stereochemistry , catalysis , polymerization , polymer
A sequential enyne‐metathesis/Diels–Alder strategy is reported for the synthesis of a new class of sugar–oxasteroid–quinone hybrid molecules. 1,2:5,6‐Di‐ O ‐isopropylidine‐ d ‐glucose was chosen as a chiral‐pool starting material. Various sugar‐derived enynes were synthesised from the common starting material. Dienes derived from these enynes were treated with various quinone dienophiles under Diels–Alder reaction conditions to give a library of sugar–oxasteroid–quinone hybrids.