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Synthetic Studies toward (±)-Furanocembranoid 1: Construction of the Acyclic Carbon Framework
Author(s) -
Chada Raji Reddy,
Siddique Z. Mohammed
Publication year - 2018
Publication title -
acs omega
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.779
H-Index - 40
ISSN - 2470-1343
DOI - 10.1021/acsomega.8b02328
Subject(s) - annulation , salt metathesis reaction , furan , metathesis , chemistry , combinatorial chemistry , stereochemistry , ring closing metathesis , organic chemistry , catalysis , polymer , polymerization
Herein, we report the synthesis of the entire acyclic carbon framework toward (±)-furanocembranoid 1 via the longest linear sequence of 12 steps from commercially available linalool and diethyl 2-isopropylmalonate. Key to the success of this synthetic approach is a silver-catalyzed enyne-annulation reaction for the formation of 2,4-disubstituted furan motif of unique furanocembranoid 1, isolated from Croton oblongifolius . Construction of macrocycle has also been explored using the ring-closing metathesis reaction.

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