title: A Highly Convergent and Biomimetic Total Synthesis of Portentol.
abstract: An efficient total synthesis of the unusual polyketide portentol is reported. Three boron aldol reactions were used to assemble the linear carbon chain of the natural product, which contains two challenging anti-anti stereotriads. A biomimetic double cyclization cascade, triggered by an oxidation, then afforded portentol and its known dehydration product, anhydroportentol. The biosynthesis of portentol and the biosynthetic relevance of our key step are discussed.
authors.affiliation: Department of Chemistry and Center for Integrated Protein Science, Ludwig-Maximilians-Universität München , Butenandtstrasse 5-13, 81377 München, Germany.
authors.forename: Bichu
authors.initials: B
authors.lastname: Cheng
authors.affiliation: Department of Chemistry and Center for Integrated Protein Science, Ludwig-Maximilians-Universität München , Butenandtstrasse 5-13, 81377 München, Germany.
authors.forename: Dirk
authors.initials: D
authors.lastname: Trauner
mesh_terms: D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D040761:Biomimetic Materials / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D018360:Crystallography, X-Ray; D003500:Cyclization; D008958:Models, Molecular; D008968:Molecular Conformation; D010084:Oxidation-Reduction; D011714:Pyrans / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism
chemical_list: D001688:Biological Products; D011714:Pyrans; D013141:Spiro Compounds; C571246:portentol