Studies on the Synthesis of Elegan-Type Linear Diterpenes: The Efficient Total Syntheses of Eleganolone, Eleganolone Acetate, Elegandiol, Eleganonal, and Epoxyeleganolone
- 1 January 1998
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of Natural Products
- Vol. 61 (1) , 92-95
- https://doi.org/10.1021/np970227g
Abstract
The first total syntheses of five elegan-type linear diterpeneseleganolone (1), eleganolone acetate (2), elegandiol (3), eleganonal (4), and epoxyeleganolone (5)were accomplished starting from (E,E)-farnesol (6) via four to six steps, successively, with high overall yield. The key step was the alkylation reaction of silyl cyanide with allylic iodide.Keywords
This publication has 11 references indexed in Scilit:
- Relaxing Activity of Two Linear Diterpenes fromCystoseira brachycarpavar.balearicaon the Contractions of Intestinal PreparationsPlanta Medica, 1995
- Crude Extracts and Two Linear Diterpenes fromCystoseira balearicaand their ActivityPlanta Medica, 1993
- Stereo- and enantioselective total synthesis of sarcophytol-ATetrahedron Letters, 1990
- Labdane diterpenes from Brickellia glomerata☆Phytochemistry, 1987
- A novel acyclic diterpene from the brown alga bifurcaria bifurcataPhytochemistry, 1983
- A geranylacetone derivative from the brown alga Cystoseira crinitaPhytochemistry, 1980
- Epoxyeleganolone et eleganediol, deux nouveaux diterpenes de bifurcaria bifurcata ross (cystoseiracees)Tetrahedron Letters, 1980
- Eleganolone nouveau cetol diterpenique lineaire de la pheophycee Cystoseira elegansPhytochemistry, 1978
- Synthesis of a tantalum pentahydride complexJournal of the American Chemical Society, 1973
- CIV. Total synthesis of the structural gene for an alanine transfer ribonucleic acid from yeast. Chemical synthesis of an icosadeoxynucleotide corresponding to the nucleotide sequence 21 to 40Journal of Molecular Biology, 1972