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Rogiolenyne D, the likely immediate precursor of rogiolenyne A and B, branched C15 acetogenins isolated from the red seaweed Laurencia microcladia of II Rogiolo. Conformation and absolute configuration in the whole series

✍ Scribed by Graziano Guella; Ines Mancini; Giuseppe Chiasera; Francesco Pietra

Publisher
John Wiley and Sons
Year
1992
Tongue
German
Weight
467 KB
Volume
75
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

It is shown that in the red seaweed Jaurencia microcladia, collected in the Mediterranean off the torrent Il Rogiolo, the new branched C~15~ acetogenin rogiolenyne D ( = (+)‐(__2__S,3__S,7__R))‐3‐(bromomethyl)‐7‐[(Z)‐1‐chlorohexen‐3‐en‐5‐nyyl)]‐2‐ethyl‐2,3,6,7‐tetrahydrooxepin; (+)‐−3 co‐occurs with the already reported rogiolenyne A ((−)‐1) and B ((−)‐2a, suggesting the lineage (+)‐3→(−)‐1(−)‐2a,Which is realized here chemically. The relative configurations are established via NMR analysis and chemical transformations as regards the seven‐membered ring, while recourse is made to conformational analysis for the side chain. The absolute configuration is established via the Mosher's NMR method applied to the MPTA esters of (−)‐2a.

📜 SIMILAR VOLUMES

Rogiolenyne A, B, and C: The First Branc
Rogiolenyne A, B, and C: The First Branched Marine C15 Acetogenins. Isolation from the Red Seaweed Laurencia microcladia or the Sponge Spongia zimocca of II Rogiolo
✍ Graziano Guella; Francesco Pietra 📂 Article 📅 1991 🏛 John Wiley and Sons 🌐 German ⚖ 414 KB

## Abstract It is shown here that the red seaweed __Laurencia microcladia__, collected off the torrent II Rogiolo, south of Livorno, contains rogiolenyne A (= __(−)‐(1__R\*,__2__S\*,__3__R\*,__5__S\*,__7__S\*__)‐2‐(bromomethyl)‐5‐[(__Z__)‐1‐chlorohex‐3‐en‐5‐ynyl]‐3‐ethyl‐4,8‐dioxabicyclo[5.1.0]octa

On the unusual propensity by the red sea
On the unusual propensity by the red seaweed Laurencia microcladia of II Rogiolo to form C15 oxepanes: Isolation of rogioloxepane A, B, C, and their likely biogenetic acyclic precursor, prerogioloxepane
✍ Graziano Guella; Ines Mancini; Giuseppe Chiasera; Francesco Pietra 📂 Article 📅 1992 🏛 John Wiley and Sons 🌐 German ⚖ 742 KB

## Abstract It is shown here that the red seaweed __Laurencia microcladia__ KÜTZNING, collected in the Mediterranean off the torrent Il rogiolo, contains the C~15~ acetogenin rogioloxepane A ( = (+)‐__(2__R,__7__R__)‐2‐(1‐bromopropyl)‐7‐[(__Z__)‐1‐chlorohex‐3‐en‐5‐ynyl]‐2,3,6,7‐tetrahydrooxepin__;