Relative stereochemistries of the ether rings and sugar moieties in durinskiol A

Tetrahedron Letters

Volumn 48, Issue 19, 2007, Pages 3429-3432

  Kita, Masaki ^a   Roy, Michael C ^a   Siwu, Eric R O ^a   Noma, Isao ^a   Takiguchi, Takahiro ^a   Yamada, Kaoru ^a   Koyama, Tomoyuki ^a   Iwashita, Takeshi ^b   Wakamiya, Atsushi ^a   Uemura, Daisuke ^a  

^a NAGOYA UNIVERSITY   (Japan)

^b SUNTORY INSTITUTE FOR BIOORGANIC RESEARCH   (Japan)

Author keywords

Configuration determination; Glycosides; Molecular modeling; Natural products; Super carbon chain compounds

Indexed keywords

DURINSKIOL A; ETHER; POLYOL; SUGAR; UNCLASSIFIED DRUG;

AB INITIO CALCULATION; ARTICLE; DINOFLAGELLATE; DURINSKIA; MOLECULAR MODEL; MOLECULAR WEIGHT; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

DINOPHYCEAE;

EID: 34147156580     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.03.039     Document Type: Article

References (7)

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5. *) whose A-ring was flipped was also conceivable (see below). However, the bis-equatorial C-O conformation in the 6,5,6-bis-spiroacetal ring may be unfavorable from the viewpoint of anomeric effects, and the lack of NOEs regarding H17/H22 and H19/H22 disagreed with such a conformation. {A figure is presented}.
6. 6 as implemented within MacroModel.
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