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An Enantioselective Approach to Pinguisane Sesquiterpenes: Total Synthesis of (–)‐Pinguisenol and (–)‐Isonaviculol
Author(s) -
Yadav Jhillu Singh,
Singh Shweta,
Das Saibal
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.201700395
Subject(s) - enantioselective synthesis , chemistry , cyclopropanation , cyclopropane , total synthesis , regioselectivity , yield (engineering) , ketone , olefin fiber , stereoselectivity , organic chemistry , stereochemistry , catalysis , ring (chemistry) , materials science , metallurgy
A short and efficient enantioselective approach to pinguisane‐type sesquiterpenes has been developed starting from a Hajos–Parrish‐type ketone. This led to the first total syntheses of isonaviculol (10 steps, 6.6 % overall yield) and natural pinguisenol (9 steps, 12 % overall yield). The key reactions were regioselective thioketal protection, stereoselective cyclopropanation using Furukawa's protocol, diastereoselective hydrogenation of an olefin using a Thalesnano H‐Cube Pro flow reactor, Li/liquid NH 3 mediated cyclopropane reduction, and a PCC‐mediated 1,3‐oxidative transposition sequence.