Literature DB >> 19865690

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

Subham Mahapatra1, Rich G Carter.   

Abstract

Synthesis of the C(7)-C(20) subunit of amphidinolides C and F has been accomplished utilizing a Me(3)Al-mediated ring opening of a vinyl iodide/allylic epoxide to establish the C(12,13)anti stereochemistry, an organolithium coupling/olefination sequence to construct the C(9)-C(11) diene moiety and a sulfone alkylation/hydroxylation strategy to join the C(7)-C(14) and C(15)-C(20) fragments.

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Year:  2009        PMID： 19865690      PMCID： PMC2830907          DOI： 10.1039/b916744g

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN： 1477-0520            Impact factor:   3.876


  28 in total

1.  Absolute stereochemistry of amphidinolide C.

Authors:  T Kubota; M Tsuda; J Kobayashi
Journal:  Org Lett       Date:  2001-05-03       Impact factor: 6.005

2.  Unified synthesis of C19-C26 subunits of amphidinolides B1, B2, and B3 by exploiting unexpected stereochemical differences in Crimmins' and Evans' aldol reactions.

Authors:  Wei Zhang; Rich G Carter; Alexandre F T Yokochi
Journal:  J Org Chem       Date:  2004-04-02       Impact factor: 4.354

3.  Synthetic studies on amphidinolide B1.

Authors:  Amit K Mandal; John S Schneekloth; Kouji Kuramochi; Craig M Crews
Journal:  Org Lett       Date:  2006-02-02       Impact factor: 6.005

4.  Amphidinolide F, a new cytotoxic macrolide from the marine dinoflagellate Amphidinium sp.

Authors:  J Kobayashi; M Tsuda; M Ishibashi; H Shigemori; T Yamasu; H Hirota; T Sasaki
Journal:  J Antibiot (Tokyo)       Date:  1991-11       Impact factor: 2.649

5.  R3Al-R'3SiOTf: novel and powerful reagent system for stereospecific alkylation-silylation reactions of epoxides.

Authors:  Ponnusamy Shanmugam; Masaaki Miyashita
Journal:  Org Lett       Date:  2003-09-04       Impact factor: 6.005

6.  A novel approach to the taxane BC ring system through formation of alpha-ketol by oxidative removal of the phenylsulfonyl group with subsequent in situ oxidation.

Authors:  H Fujishima; H Takeshita; M Toyota; M Ihara
Journal:  J Org Chem       Date:  2001-04-06       Impact factor: 4.354

7.  Building a small polypropionate library. Synthesis of all possible stereotetrads (building blocks for polyketide synthesis) from furan.

Authors:  O Arjona; R Menchaca; J Plumet
Journal:  J Org Chem       Date:  2001-04-06       Impact factor: 4.354

8.  Synthesis of the C11-C29 fragment of amphidinolide F.

Authors:  J Brad Shotwell; William R Roush
Journal:  Org Lett       Date:  2004-10-14       Impact factor: 6.005

9.  Amphidinolides and its related macrolides from marine dinoflagellates.

Authors:  Jun'ichi Kobayashi
Journal:  J Antibiot (Tokyo)       Date:  2008-05       Impact factor: 2.649

10.  Total syntheses of amphidinolides B1, B4, G1, H1 and structure revision of amphidinolide H2.

Authors:  Alois Fürstner; Laure C Bouchez; Louis Morency; Jaques-Alexis Funel; Vilnis Liepins; François-Hugues Porée; Ryan Gilmour; Daniel Laurich; Florent Beaufils; Minoru Tamiya
Journal:  Chemistry       Date:  2009       Impact factor: 5.236
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  5 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.  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

3.  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

4.  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

5.  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
  5 in total

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