title: Tandem Allylboration-Prins Reaction for the Rapid Construction of Substituted Tetrahydropyrans: Application to the Total Synthesis of (-)-Clavosolide A.
abstract: Tetrahydropyrans are common motifs in natural products and have now been constructed with high stereocontrol through a three-component allylboration-Prins reaction sequence. This methodology has been applied to a concise (13 steps) and efficient (14 % overall yield) synthesis of the macrolide (-)-clavosolide A. The synthesis also features an early stage glycosidation reaction to introduce the xylose moiety and a lithiation-borylation reaction to attach the cyclopropyl-containing side chain.
authors.affiliation: School of Chemistry, University of Bristol, Cantock's Close, Bristol, BS8 1TS, UK.
authors.forename: Alba
authors.identifier: http://orcid.org/0000-0003-2754-270X
authors.initials: A
authors.lastname: Millán
authors.affiliation: School of Chemistry, University of Bristol, Cantock's Close, Bristol, BS8 1TS, UK.
authors.forename: James R
authors.initials: JR
authors.lastname: Smith
authors.affiliation: School of Chemistry, University of Bristol, Cantock's Close, Bristol, BS8 1TS, UK.
authors.forename: Jack L-Y
authors.initials: JL
authors.lastname: Chen
authors.affiliation: School of Chemistry, University of Bristol, Cantock's Close, Bristol, BS8 1TS, UK. v.aggarwal@bristol.ac.uk.
authors.forename: Varinder K
authors.identifier: http://orcid.org/0000-0003-0344-6430
authors.initials: VK
authors.lastname: Aggarwal
keywords: Prins reaction; allylboration; lithiation-borylation; natural products; total synthesis