Literature DB >> 11348235

Absolute stereochemistry of amphidinolide C.

T Kubota1, M Tsuda, J Kobayashi.   

Abstract

[structure in text] The absolute configurations at 12 chiral centers in amphidinolide C (1), a potent cytotoxic 25-membered macrolide isolated from a marine dinoflagellate Amphidinium sp., were determined to be 3S, 4R, 6R, 7R, 8R, 12R, 13S, 16S, 20R, 23R, 24R, and 29S by combination of NMR analyses, degradation experiments, and synthesis of the C-1-C-7 segment.

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Year:  2001        PMID: 11348235     DOI: 10.1021/ol015741z

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  9 in total

1.  A formal synthesis of the C1-C9 fragment of amphidinolide C employing the Tamaru reaction.

Authors:  Mahesh P Paudyal; Nigam P Rath; Christopher D Spilling
Journal:  Org Lett       Date:  2010-07-02       Impact factor: 6.005

2.  Amphidinolide B: total synthesis, structural investigation, and biological evaluation.

Authors:  Liang Lu; Wei Zhang; Sangkil Nam; David A Horne; Richard Jove; Rich G Carter
Journal:  J Org Chem       Date:  2013-02-13       Impact factor: 4.354

3.  Studies toward the Synthesis of Amphidinolide C1: Stereoselective Construction of the C(1)-C(15) Segment.

Authors:  Sheila Namirembe; Lu Yan; James P Morken
Journal:  Org Lett       Date:  2020-11-12       Impact factor: 6.005

4.  Enantioselective total synthesis of amphidinolide F.

Authors:  Subham Mahapatra; Rich G Carter
Journal:  Angew Chem Int Ed Engl       Date:  2012-07-05       Impact factor: 15.336

5.  Convergent Synthesis of the C1-C29 Framework of Amphidinolide F.

Authors:  Filippo Romiti; Ludovic Decultot; J Stephen Clark
Journal:  J Org Chem       Date:  2022-06-08       Impact factor: 4.198

6.  Stereoselective syntheses of the C(1)-C(9) fragment of amphidinolide C.

Authors:  Robert H Bates; J Brad Shotwell; William R Roush
Journal:  Org Lett       Date:  2008-09-11       Impact factor: 6.005

7.  Efficient synthesis of the C(7)-C(20) subunit of amphidinolides C and F.

Authors:  Subham Mahapatra; Rich G Carter
Journal:  Org Biomol Chem       Date:  2009-09-16       Impact factor: 3.876

8.  Synthesis of the C(18)-C(34) fragment of amphidinolide C and the C(18)-C(29) fragment of amphidinolide F.

Authors:  Sudeshna Roy; Christopher D Spilling
Journal:  Org Lett       Date:  2010-10-28       Impact factor: 6.005

9.  Exploiting hidden symmetry in natural products: total syntheses of amphidinolides C and F.

Authors:  Subham Mahapatra; Rich G Carter
Journal:  J Am Chem Soc       Date:  2013-07-11       Impact factor: 15.419

  9 in total

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