Synthesis of marine polycyclic polyethers via endo-selective epoxide-opening cascades.
The proposed biosynthetic pathways to ladder polyethers of polyketide origin and oxasqualenoids of terpenoid origin share a dramatic epoxide-opening cascade as a key step. Polycyclic structures generated in these biosynthetic pathways display biological effects ranging from potentially therapeutic properties to extreme lethality. Much of the structural complexity of ladder polyether and oxasqualenoid natural products can be traced to these hypothesized cascades. In this review we summarize how such epoxide-opening cascade reactions have been used in the synthesis of ladder polyethers and oxasqualenoid natural products.
Vilotijevic
Ivan
I
Department of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Avenue, Cambridge, MA 02139, USA.
Jamison
Timothy F
TF
D000818:Animals; D001688:Biological Products / Q000097:blood / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D004852:Epoxy Compounds / Q000737:chemistry*; D004987:Ethers / Q000138:chemical synthesis* / Q000737:chemistry; D056890:Eukaryota / Q000737:chemistry; D008386:Marine Biology; D010944:Plants / Q000737:chemistry; D011161:Porifera / Q000737:chemistry; D011714:Pyrans / Q000138:chemical synthesis / Q000737:chemistry
D001688:Biological Products; D004852:Epoxy Compounds; D004987:Ethers; D011714:Pyrans
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