Abstract
The construction of strictly the (S)-hexahydroxydiphenyl (HHDP) unit via biomimetic cyclization of suitably protected glucose-derived digalloyl esters has been achieved in good yield. Studies on substrates of increasing complexity utilizing a range of oxidants (Pb(OAc)4, VOF3, Tl2O3) have helped define the scope and limitations of this approach to ellagitannin synthesis. Computer modeling of key cyclization precursors helped elucidate the molecular-level structural details which undergird the Haslam/Schmidt biosynthesis model for this class of naturally occurring secondary plant metabolites.
| Original language | English (US) |
|---|---|
| Pages (from-to) | 3357-3366 |
| Number of pages | 10 |
| Journal | Journal of the American Chemical Society |
| Volume | 116 |
| Issue number | 8 |
| DOIs | |
| State | Published - Apr 1 1994 |
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All Science Journal Classification (ASJC) codes
- Catalysis
- Chemistry(all)
- Biochemistry
- Colloid and Surface Chemistry
Cite this
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Ellagitannin Chemistry. Preparative and Mechanistic Studies of the Biomimetic Oxidative Coupling of Galloyl Esters. / Feldman, Ken S.; Ensel, Susan M.
In: Journal of the American Chemical Society, Vol. 116, No. 8, 01.04.1994, p. 3357-3366.Research output: Contribution to journal › Article
TY - JOUR
T1 - Ellagitannin Chemistry. Preparative and Mechanistic Studies of the Biomimetic Oxidative Coupling of Galloyl Esters
AU - Feldman, Ken S.
AU - Ensel, Susan M.
PY - 1994/4/1
Y1 - 1994/4/1
N2 - The construction of strictly the (S)-hexahydroxydiphenyl (HHDP) unit via biomimetic cyclization of suitably protected glucose-derived digalloyl esters has been achieved in good yield. Studies on substrates of increasing complexity utilizing a range of oxidants (Pb(OAc)4, VOF3, Tl2O3) have helped define the scope and limitations of this approach to ellagitannin synthesis. Computer modeling of key cyclization precursors helped elucidate the molecular-level structural details which undergird the Haslam/Schmidt biosynthesis model for this class of naturally occurring secondary plant metabolites.
AB - The construction of strictly the (S)-hexahydroxydiphenyl (HHDP) unit via biomimetic cyclization of suitably protected glucose-derived digalloyl esters has been achieved in good yield. Studies on substrates of increasing complexity utilizing a range of oxidants (Pb(OAc)4, VOF3, Tl2O3) have helped define the scope and limitations of this approach to ellagitannin synthesis. Computer modeling of key cyclization precursors helped elucidate the molecular-level structural details which undergird the Haslam/Schmidt biosynthesis model for this class of naturally occurring secondary plant metabolites.
UR - http://www.scopus.com/inward/record.url?scp=0001333615&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0001333615&partnerID=8YFLogxK
U2 - 10.1021/ja00087a022
DO - 10.1021/ja00087a022
M3 - Article
VL - 116
SP - 3357
EP - 3366
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
SN - 0002-7863
IS - 8
ER -