Total synthesis and biological evaluation of neodysiherbaine A and analogues.

Total synthesis and biological evaluation of neodysiherbaine A and analogues. Research Abstract Details 

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Total synthesis and biological evaluation of neodysiherbaine A and analogues. Abstract Text:

Muneo Shoji,Nobuyuki Akiyama,Koichi Tsubone,L Leanne Lash,James M Sanders,Geoffrey T Swanson,Ryuichi Sakai,Keiko Shimamoto,Masato Oikawa,Makoto Sasaki,

Dysiherbaine (1) and its congener neodysiherbaine A (2) are naturally occurring excitatory amino acids with selective and potent agonistic activity for ionotropic glutamate receptors. We describe herein the total synthesis of 2 and its structural analogues 3-8. Advanced key intermediate 16 was employed as a branching point to assemble a series of these analogues 3-8 with respect to the C8 and C9 functionalities, which would not have been accessible through manipulations of the natural product itself. The synthesis of key intermediate 16 features (i) stereocontrolled C-glycosylation to set the C6 stereocenter, (ii) concise synthesis of the bicyclic ether skeleton through chemo- and stereoselective dihydroxylation of the exo-olefin and stereoselective epoxidation of the endo-olefin, followed by epoxide ring opening/5-exo ring closure, and (iii) catalytic asymmetric hydrogenation of enamide ester to construct the amino acid appendage. A preliminary biological evaluation of analogues for their in vivo toxicity against mice and binding affinity for glutamate receptors showed that both the type and stereochemistry of the C8 and C9 functional groups affected the subtype selectivity of dysiherbaine analogues for members of the kainic acid receptor family.

Total synthesis and biological evaluation of neodysiherbaine A and analogues. Publishing Authors By Initials

M Shoji,N Akiyama,K Tsubone,LL Lash,JM Sanders,GT Swanson,R Sakai,K Shimamoto,M Oikawa,M Sasaki,

For similar biochemical phenomena, metabolism, and nutrition: biochemical phenomena: structure-activity relationship research abstracts see: biochemical phenomena, metabolism, and nutrition: biochemical phenomena: structure-activity relationship research

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Total synthesis and biological evaluation of neodysiherbaine A and analogues. Journal Published:

PUBLICATION TYPE: Research Support, Non-U.S. Gov

Journal: The Journal of organic chemistry

VOLUME: 71

Page Numbers: 5208-20

Journal Abbreviation: J. Org. Chem.

ISSN: 0022-3263

DAY: 7

MONTH: Jul

YEAR: 2006

Total synthesis and biological evaluation of neodysiherbaine A and analogues. Information

Number of References:

LANGUAGE: eng

NlmUniqueID: 2985193

Total synthesis and biological evaluation of neodysiherbaine A and analogues. Keywords Mesh Terms:

KEYWORDS: Structure-Activity Relationship

MESH TERMS: chemically induced

Chemical & Substance for Abstract: Total synthesis and biological evaluation of neodysiherbaine A and analogues. Information

Substance Name: Alanine

Registry Number: 56-41-7

Grant and Affiliation Information for Total synthesis and biological evaluation of neodysiherbaine A and analogues.

AFFILIATION: Laboratory of Biostructural Chemistry, Graduate School of Life Sciences, Tohoku University, Sendai 981-8555, Japan.

Country: United States

AGENCY: United States NINDS

GRANT: R01 NS 44322

ACRONYM: NS

MEDLINETA: J Org Chem

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