Synthetic strategies of marine polycyclic ethers via intramolecular allylations: linear and convergent approaches.
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).
Kadota
Isao
I
Research and Analytical Center for Giant Molecules and Department of Chemistry, Graduate School of Science, Tohoku University, Sendai 980-8578, Japan.
Yamamoto
Yoshinori
Y
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
D000447:Aldehydes; D000498:Allyl Compounds; D004988:Ethers, Cyclic; D011083:Polycyclic Compounds