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The Total Synthesis of (±)‐Naupliolide: A Tetracyclic Sesquiterpene Lactone
Author(s) -
Abe Hideki,
Morishita Tomoyuki,
Yoshie Toshihiro,
Long Kérya,
Kobayashi Toyoharu,
Ito Hisanaka
Publication year - 2016
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201600055
Subject(s) - cyclopropanation , cyclopropane , total synthesis , chemistry , acetal , sesquiterpene , aldehyde , metathesis , stereochemistry , ring (chemistry) , lactone , radical cyclization , allyl alcohol , epoxide , ring closing metathesis , ketone , organic chemistry , catalysis , polymer , polymerization
The first total synthesis of (±)‐naupliolide has been achieved. The synthetic method includes a Simmons–Smith cyclopropanation of an allyl alcohol, diastereoselective cleavage of a benzylidene acetal group, radical cyclization of an aldehyde with a cyclopropane ring, and construction of an eight‐membered ring by ring‐closing metathesis.