Synthesis of Sphingosine Relatives, XII Synthesis and Absolute Configuration of the Two Epimeric Aliphatic Amino Alcohols [5E, 7E)-2-Amino-5,7-tetradecadien-3-ols] Isolated from a Sponge,Xestospongia sp.
✍ Scribed by Mori, Kenji ;Matsuda, Hiroyuki
- Publisher
- John Wiley and Sons
- Year
- 1992
- Tongue
- English
- Weight
- 717 KB
- Volume
- 1992
- Category
- Article
- ISSN
- 0947-3440
No coin nor oath required. For personal study only.
✦ Synopsis
Abstract
(2__S__, 3__S__, 5__E__, 7__E__)‐ and (2__S__, 3__R__, 5__E__, 7__E__)‐2‐Amino‐5,7‐tetradecadien‐3‐ol [(S)‐1a and (S)‐1b], which were proposed as the structures of epimeric amino alcohols isolated from a marine sponge, and their two enantiomers were synthesized from (S)‐ and (R)‐alanine, respectively. The high‐field ^1^H‐NMR spectra of the diacetyl derivatives of 1a, b were identical with those of the derivatives of naturally occurring amino alcohols. However, the absolute configurations of the natural products were corrected as (2__R__) by comparing the optical rotations of natural products with those of the synthetic products.