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Sesterterpenes: An Emerging Group of Metabolites from Marine and Terrestrial Organisms

  • P. Crews
  • S. Naylor
Part of the Fortschritte der Chemie organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products book series (FORTCHEMIE (closed), volume 48)

Abstract

Naturally occurring sesterterpenes were first encountered less than thirty years ago, and as a consequence they are often viewed as a rare category of natural products. The first sesterterpenes, isolated during the late 1950’s, included ophiobolin A which was present in crude extracts studied by Orsenigo(1) and gascardic acid reported by Brochere-Ferreoland Polonsky(2). No structures were determined initially for either of these. However, the complete tricarbocyclic skeleton for ophiobolin A along with the absolute stereochemistry at eight chiral sites shown in formula (75) (see Table 6) was elucidated in 1965 after an X-ray study by Nozoeand coworkers (3). In the same year structure (i), featuring a polycarbocyclic frame, was announced for gascardic acid by Arigoniand Scartazzini(4,5). Two out of the five elements of its relative stereochemistry were defined, whereas the remaining centers were pinned down in representation (85) by Clardyand Boeckmanonly after an X-ray crystallographic study of gascardic acid dicyclohexylammonium salt (6)*. Lagging slightly behind the above was the discovery and characterization of the first acyclic sesterterpene geranylnerolidol (2) in 1968 by Nozoeand coworkers (7).

Keywords

Absolute Configuration Marine Sponge Carbon Skeleton Total Synthesis Terrestrial Organism 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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Copyright information

© Springer-Verlag/Wien 1985

Authors and Affiliations

  • P. Crews
    • 1
  • S. Naylor
    • 1
  1. 1.Thimann Laboratories and Center for Coastal Marine StudiesUniversity of CaliforniaSanta CruzUSA

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