Literature DB >> 16953609

Progressive-convergent elucidation of stereochemistry in complex polyols. The absolute configuration of (-)-sagittamide A.

Sarah C Lievens1, Tadeusz F Molinski.   

Abstract

The absolute stereostructure of sagittamide A (1), a O-hexacetyl long-chain hexahydroxy-alpha,omega-dicarboxylic acid, was assigned using a progressive-convergent approach that integrates three powerful regimens for stereochemical analysis of acyclic natural products: J-based analysis, 13C NMR universal database comparisons, and exciton coupling circular dichroism.

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Year:  2006        PMID： 16953609      PMCID： PMC3340292          DOI： 10.1021/ja063735y

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  5 in total

1.  Toward creation of a universal NMR database for stereochemical assignment: complete structure of the desertomycin/oasomycin class of natural products.

Authors:  Y Kobayashi; C H Tan; Y Kishi
Journal:  J Am Chem Soc       Date:  2001-03-07       Impact factor: 15.419

2.  Toward the creation of NMR databases in chiral solvents: bidentate chiral NMR solvents for assignment of the absolute configuration of acyclic secondary alcohols.

Authors:  Yoshihisa Kobayashi; Nobuyuki Hayashi; Yoshito Kishi
Journal:  Org Lett       Date:  2002-02-07       Impact factor: 6.005

3.  Toward creation of a universal NMR database for the stereochemical assignment of acyclic compounds: the case of two contiguous propionate units.

Authors:  Y Kobayashi; J Lee; K Tezuka; Y Kishi
Journal:  Org Lett       Date:  1999-12-30       Impact factor: 6.005

4.  Sagittamides A and B. Polyacetoxy long-chain acyl amino acids from a didemnid ascidian.

Authors:  Sarah C Lievens; Tadeusz F Molinski
Journal:  Org Lett       Date:  2005-05-26       Impact factor: 6.005

5.  Stereochemical Determination of Acyclic Structures Based on Carbon-Proton Spin-Coupling Constants. A Method of Configuration Analysis for Natural Products.

Authors:  Nobuaki Matsumori; Daisuke Kaneno; Michio Murata; Hideshi Nakamura; Kazuo Tachibana
Journal:  J Org Chem       Date:  1999-02-05       Impact factor: 4.354
  5 in total
  2 in total

1.  INTEGRATED APPROACHES TO THE CONFIGURATIONAL ASSIGNMENT OF MARINE NATURAL PRODUCTS.

Authors:  Tadeusz F Molinski; Brandon I Morinaka
Journal:  Tetrahedron       Date:  2012-11-18       Impact factor: 2.457

2.  A further contribution to the study of sagittamide A: synthesis of a pivotal intermediate belonging to a rare L-series.

Authors:  Anne Humbert; Karen Plé; Dominique Harakat; Agathe Martinez; Arnaud Haudrechy
Journal:  Molecules       Date:  2012-06-25       Impact factor: 4.411
  2 in total

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