title: Contemporary Strategies for the Synthesis of Tetrahydropyran Derivatives: Application to Total Synthesis of Neopeltolide, a Marine Macrolide Natural Product.
abstract: Tetrahydropyrans are structural motifs that are abundantly present in a range of biologically important marine natural products. As such, significant efforts have been paid to the development of efficient and versatile methods for the synthesis of tetrahydropyran derivatives. Neopeltolide, a potent antiproliferative marine natural product, has been an attractive target compound for synthetic chemists because of its complex structure comprised of a 14-membered macrolactone embedded with a tetrahydropyran ring, and twenty total and formal syntheses of this natural product have been reported so far. This review summarizes the total and formal syntheses of neopeltolide and its analogues, highlighting the synthetic strategies exploited for constructing the tetrahydropyran ring.
authors.affiliation: Graduate School of Life Sciences, Tohoku University, 2-1-1 Katahira, Aoba-ku, Sendai 980-8577, Japan. hfuwa@m.tohoku.ac.jp.
authors.forename: Haruhiko
authors.initials: H
authors.lastname: Fuwa
mesh_terms: D000818:Animals; D001688:Biological Products / Q000737:chemistry*; D006801:Humans; D007783:Lactones / Q000737:chemistry; D018942:Macrolides / Q000737:chemistry*; D011714:Pyrans / Q000737:chemistry*
chemical_list: D001688:Biological Products; D007783:Lactones; D018942:Macrolides; D011714:Pyrans; C519136:neopeltolide
keywords: hetero-Diels-Alder cycloadditions; oxa-Michael reactions; oxocarbenium ions; oxymercurations; palladium-catalyzed alkoxycarbonylations; radical cyclizations; ring-closing metathesis; synthetic methods; tetrahydropyrans