Absolute stereochemistry of ibhayinol from a South African sea hare.
The absolute stereochemistry of the tricyclic, sesquiterpene ibhayinol (5) extracted from the sea hare Aplysia dactylomela, collected in Algoa Bay, South Africa, was established as 1S, 3S, 4S, 6R, 7S, 10R, 11S from a single-crystal X-ray diffraction experiment. The structure of ibhayinol suggested that 8-dehydroxy-1-deacetylalgoane (7) might be a biosynthetic precursor of this compound.
Copley
Royston C B
RC
Department of Chemistry, Rhodes University, Grahamstown, South Africa.
Davies-Coleman
Michael T
MT
Edmonds
David R
DR
Faulkner
D John
DJ
McPhail
Kerry L
KL
D000818:Animals; D001048:Aplysia / Q000737:chemistry*; D018360:Crystallography, X-Ray; D008968:Molecular Conformation; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D012717:Sesquiterpenes / Q000737:chemistry / Q000302:isolation & purification*; D013019:South Africa
C457211:8-dehydroxy-1-deacetylalgoane; D012717:Sesquiterpenes; C457212:algoane; C457210:ibhayinol