title: Synthetic strategies of marine polycyclic ethers via intramolecular allylations: linear and convergent approaches.
abstract: Strategies for the synthesis of polycyclic ethers based on intramolecular allylations are overviewed. The intramolecular condensation of allylic stannanes and aldehydes is a powerful tool for the synthesis of oxepane derivatives. The reaction is successfully applied to the iterative total synthesis of hemibrevetoxin B (2). Further, the intramolecular allylation of alpha-acetoxy ethers provides an efficient method for the convergent synthesis of polycyclic ethers. The usefulness of the latter strategy is demonstrated in the convergent total synthesis of gambierol (4).
authors.affiliation: Research and Analytical Center for Giant Molecules and Department of Chemistry, Graduate School of Science, Tohoku University, Sendai 980-8578, Japan.
authors.forename: Isao
authors.initials: I
authors.lastname: Kadota
authors.forename: Yoshinori
authors.initials: Y
authors.lastname: Yamamoto
mesh_terms: D000447:Aldehydes / Q000737:chemistry; D000498:Allyl Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D004988:Ethers, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009792:Oceans and Seas; D011083:Polycyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000447:Aldehydes; D000498:Allyl Compounds; D004988:Ethers, Cyclic; D011083:Polycyclic Compounds