Total synthesis of calditol: structural clarification of this typical component of Archaea order Sulfolobales.
The original structure of calditol--that is, an open-chain branched nonitol--has recently been questioned by various research groups and cyclopentane-based structures have been proposed. To unambiguously clear up this confusion, four isomeric cyclopentane candidates 26-29 have been synthesized. Of these, compound 27 was found to be fully identical to the natural product present in Sulfolobus solfataricus (A.T.C.C. 49155). The synthesis of 27 uses a samarium-diiodide-induced pinacolization reaction of the ketoaldehyde 15 as the critical step.
Blériot
Yves
Y
Département de Chimie, Associé au CNRS Ecole Normale Supérieure, Paris, France.
Untersteller
Edouard
E
Fritz
Benoît
B
Sinaÿ
Pierre
P
D000085:Acetates / Q000138:chemical synthesis* / Q000737:chemistry; D000438:Alcohols / Q000737:chemistry; D001685:Biological Factors; D002254:Carbonates / Q000737:chemistry; D003517:Cyclopentanes / Q000138:chemical synthesis / Q000737:chemistry; D004075:Diglycerides / Q000138:chemical synthesis* / Q000737:chemistry*; D008055:Lipids / Q000737:chemistry; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D013012:Sorbitol / Q000031:analogs & derivatives / Q000737:chemistry; D013237:Stereoisomerism; D013431:Sulfates / Q000737:chemistry; D013447:Sulfites / Q000737:chemistry; D016942:Sulfolobales / Q000737:chemistry*
D000085:Acetates; D000438:Alcohols; D001685:Biological Factors; D002254:Carbonates; D003517:Cyclopentanes; D004075:Diglycerides; D008055:Lipids; D013431:Sulfates; D013447:Sulfites; C448139:calditol heptacetate; C085775:glycerol dialkyl nonitol tetraethyl ether; D013012:Sorbitol