A bioinspired approach to tri-nor-guaianes. synthesis of (-)-clavukerin A.J Nat Prod. 2006 Aug; 69(8):1234-6.JN
Abstract
A bioinspired approach to tri-nor-guaianes by degradation of the C-7 side chain of related guaia-11-enes is described. In this approach (-)-clavukerin A (1) is obtained by selective ozonolysis-Criegge rearrangement of (+)-1alphaH,7alphaH,10alphaH-guaia-4,11-dien-3-one (4) to afford 7beta-hydroxy and 7beta-acetoxy tri-nor-guaiane derivatives 6 and 7, respectively, which after elimination and deoxygenation give the title compound. The starting guaiadienone is readily obtained from commercially available santonin or (+)-dihydrocarvone.
MeSH
Pub Type(s)
Journal Article
Research Support, Non-U.S. Gov't
Language
eng
PubMed ID
16933886
Citation
Blay, Gonzalo, et al. "A Bioinspired Approach to Tri-nor-guaianes. Synthesis of (-)-clavukerin A." Journal of Natural Products, vol. 69, no. 8, 2006, pp. 1234-6.
Blay G, García B, Molina E, et al. A bioinspired approach to tri-nor-guaianes. synthesis of (-)-clavukerin A. J Nat Prod. 2006;69(8):1234-6.
Blay, G., García, B., Molina, E., & Pedro, J. R. (2006). A bioinspired approach to tri-nor-guaianes. synthesis of (-)-clavukerin A. Journal of Natural Products, 69(8), 1234-6.
Blay G, et al. A Bioinspired Approach to Tri-nor-guaianes. Synthesis of (-)-clavukerin A. J Nat Prod. 2006;69(8):1234-6. PubMed PMID: 16933886.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR
T1 - A bioinspired approach to tri-nor-guaianes. synthesis of (-)-clavukerin A.
AU - Blay,Gonzalo,
AU - García,Begoña,
AU - Molina,Eva,
AU - Pedro,José R,
PY - 2006/8/29/pubmed
PY - 2006/9/29/medline
PY - 2006/8/29/entrez
SP - 1234
EP - 6
JF - Journal of natural products
JO - J Nat Prod
VL - 69
IS - 8
N2 - A bioinspired approach to tri-nor-guaianes by degradation of the C-7 side chain of related guaia-11-enes is described. In this approach (-)-clavukerin A (1) is obtained by selective ozonolysis-Criegge rearrangement of (+)-1alphaH,7alphaH,10alphaH-guaia-4,11-dien-3-one (4) to afford 7beta-hydroxy and 7beta-acetoxy tri-nor-guaiane derivatives 6 and 7, respectively, which after elimination and deoxygenation give the title compound. The starting guaiadienone is readily obtained from commercially available santonin or (+)-dihydrocarvone.
SN - 0163-3864
UR - https://www.unboundmedicine.com/medline/citation/16933886/Cyclopeptides_of_Linum_usitatissimum_
L2 - https://doi.org/10.1021/np060184g
DB - PRIME
DP - Unbound Medicine
ER -
