title: The Total Synthesis of (±)-Naupliolide: A Tetracyclic Sesquiterpene Lactone.
abstract: 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.
authors: School of Life Sciences, Tokyo University of Pharmacy and Life Sciences, 1432-1 Horinouchi, Hachioji, Tokyo, 192-0392, Japan.
authors: Hideki
authors: H
authors: Abe
authors: School of Life Sciences, Tokyo University of Pharmacy and Life Sciences, 1432-1 Horinouchi, Hachioji, Tokyo, 192-0392, Japan.
authors: Tomoyuki
authors: T
authors: Morishita
authors: School of Life Sciences, Tokyo University of Pharmacy and Life Sciences, 1432-1 Horinouchi, Hachioji, Tokyo, 192-0392, Japan.
authors: Toshihiro
authors: T
authors: Yoshie
authors: School of Life Sciences, Tokyo University of Pharmacy and Life Sciences, 1432-1 Horinouchi, Hachioji, Tokyo, 192-0392, Japan.
authors: Kérya
authors: K
authors: Long
authors: School of Life Sciences, Tokyo University of Pharmacy and Life Sciences, 1432-1 Horinouchi, Hachioji, Tokyo, 192-0392, Japan.
authors: Toyoharu
authors: T
authors: Kobayashi
authors: School of Life Sciences, Tokyo University of Pharmacy and Life Sciences, 1432-1 Horinouchi, Hachioji, Tokyo, 192-0392, Japan. itohisa@toyaku.ac.jp.
authors: Hisanaka
authors: H
authors: Ito
keywords: cyclopropanation; lactones; radicals; ring-closing metathesis; total synthesis