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- Title
Synthesis of the Bretonins, Polyolefinic Esterified Glyceryl Ethers of an Unidentified Sponge from the North-Brittany Sea: Absolute Configuration and Novel Structure Assignment.
- Authors
Mancini, Ines; Guella, Graziano; Pietra, Francesco
- Abstract
The absolute configurations of acetylated bretonin A (= (+}-( R)- 1-[(acetoxy)methyl]-2-{[(4E, 6E, 8E)- dodeca-4,6,8- trienyl] oxy} ethyl 4- acetoxybenzoate; (−)- 1b) and isobretonin A (= (+)-(S)-3-{[( 4E, 6E, 8E)- do-deca-4,6,8-trienyl]oxy}-2-hydroxypropyl 4-hydroxybenzoate; (+)-2), previously isolated from an undetermined sponge of the North Brittany sea, were established by comparison with synthetic (+)- lb and (+)- 2, obtained from the condensation of commerical (−)-(R)-2,2-dimethyl-1,3-dioxolan-4-yl p-toluenesuifonate ((−)-( R)- 15) with a mixture of (4 E,6 E,8 E)- ( 14e) and (4 E,6 Z,8 E)-dodeca-4,6,8-trien-1-ol ( 14z). This also allowed confirming the structure and configuration of bretonin B (= (S)- 2-{[(4 E,6 Z,8 E)- dodeca-4,6,8-trienyl]oxy}-1-(hydroxy-methyl)ethyl 4-hydroxybenzoate; 3) which was also isolated from the same sponge, albeit in a too small amount for a complete study. As concerns the glyceryl ethers precursors of the bretonins, co-occurrence of the usual ( S)-con-figuration (from 1a) with the unusual ( R)-configuration (from (+)- 2)) poses intriguing biogenetic problems.
- Publication
Helvetica Chimica Acta, 1991, Vol 74, Issue 5, p941
- ISSN
0018-019X
- Publication type
Article
- DOI
10.1002/hlca.19910740504