Convergent syntheses of polycyclic ethers. Illustrations of the utility of acetal-linked intermediates

Organic & Biomolecular Chemistry
Masayuki Inoue

Abstract

One of the most characteristic and spectacular class of compounds isolated from marine sources is the polycyclic ethers. Following the initial report of the structural determination of brevetoxin B, a variety of novel polycyclic ethers have begun to surface. These natural products include ciguatoxins, gambierol, gambieric acids, yessotoxins and gymnocins, each of which exhibit distinct biological properties such as cytotoxicity and neurotoxicity, as well as antiviral and antifungal activities. Because of these intriguing biological activities and their complex molecular architecture, the total synthesis of these compounds has been pursued by many laboratories over two decades. In particular, the development of novel convergent strategies to assemble the structural fragments is crucial for the successful construction of these nano-scale molecules. This Perspective will focus on a recent convergent methodology using an acetal-linkage as a key motif. Application of this methodology culminated in the total syntheses of gambierol and ciguatoxin CTX3C.

Citations

Feb 3, 2006·Natural Product Reports·Gillian M Nicholas, Andrew J Phillips
Feb 3, 2006·Natural Product Reports·John W BluntMichèle R Prinsep
Jan 9, 2007·Biotechnology Advances·F Garcia CamachoE Molina Grima
Dec 14, 2004·Organic & Biomolecular Chemistry·Caroline V PotterMichelle Canning
Feb 12, 2008·Organic & Biomolecular Chemistry·Jonathan W BurtonAndrew B Holmes
Dec 16, 2004·Chemical Communications : Chem Comm·Caroline V PotterHelen Saxton
Aug 2, 2005·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Masahiro Hirama
Dec 14, 2004·Chemical Society Reviews·Caroline V PotterHelen Saxton
Dec 22, 2004·Accounts of Chemical Research·Masayuki Inoue, Masahiro Hirama

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