title: Total synthesis and complete structural assignment of gambieric acid A, a large polycyclic ether marine natural product.
abstract: More than thirty years after the discovery of polycyclic ether marine natural products, they continue to receive intense attention from the chemical, biological, and pharmacological communities because of their potent biological activities and highly complex molecular architectures. Gambieric acids are intriguing polycyclic ethers that exhibit potent antifungal activity with minimal toxicity against mammals. Despite the recent advances in the synthesis of this class of natural products, gambieric acids remain unconquered due to their daunting structural complexity, which poses a formidable synthetic challenge to organic chemists. This paper reviews our long-term studies on the total synthesis, complete configurational reassignment, and structure-activity relationships of gambieric acid A over the last decade.
authors.affiliation: Graduate School of Life Sciences, Tohoku University, Katahira, Aoba-ku, Sendai 980-8577, Japan. masasaki@m.tohoku.ac.jp.
authors.forename: Makoto
authors.initials: M
authors.lastname: Sasaki
authors.forename: Haruhiko
authors.initials: H
authors.lastname: Fuwa
mesh_terms: D000818:Animals; D000935:Antifungal Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D060326:Chemistry Techniques, Synthetic / Q000379:methods*; D002922:Ciguatoxins / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D004141:Dinoflagellida / Q000737:chemistry*; D004988:Ethers, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D006801:Humans; D008958:Models, Molecular; D009181:Mycoses / Q000188:drug therapy; D009369:Neoplasms / Q000188:drug therapy; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
chemical_list: D000935:Antifungal Agents; D000970:Antineoplastic Agents; D001688:Biological Products; D004988:Ethers, Cyclic; D002922:Ciguatoxins; C080898:gambieric acid A
keywords: gambieric acids; marine dinoflagellates; natural products; polycyclic ethers; total synthesis