Literature DB >> 33180502

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

Sheila Namirembe1, Lu Yan1, James P Morken1.   

Abstract

An enantioselective synthesis of the C(1)-C(15) segment of the marine natural product amphidinolide C has been accomplished by a route that includes a stereoselective boron-Wittig reaction to furnish a trisubstituted alkenylboronate. In addition, the route employs enantioselective alkene diboration to install the C(6) hydroxyl group which undergoes intramolecular conjugate addition to establish a tetrahydrofuran ring. Lastly, a catalytic Suzuki-Miyaura cross-coupling is accomplished to construct the C(9)-C(10) bond.

Entities:  

Year:  2020        PMID： 33180502      PMCID： PMC7982962          DOI： 10.1021/acs.orglett.0c03134

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


  30 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.  Gram scale synthesis of the C(18)-C(34) fragment of amphidinolide C.

Authors:  Nicholas A Morra; Brian L Pagenkopf
Journal:  Org Lett       Date:  2011-01-21       Impact factor: 6.005

3.  Stereoselective Synthesis of Trisubstituted Alkenylboron Reagents by Boron-Wittig Reaction of Ketones.

Authors:  Sheila Namirembe; Chenpeng Gao; Ryan P Wexler; James P Morken
Journal:  Org Lett       Date:  2019-05-29       Impact factor: 6.005

4.  Enhanced anti-diastereo- and enantioselectivity in alcohol-mediated carbonyl crotylation using an isolable single component iridium catalyst.

Authors:  Xin Gao; Ian A Townsend; Michael J Krische
Journal:  J Org Chem       Date:  2011-03-04       Impact factor: 4.354

5.  Efficient synthesis of the C(1)-C(9) fragment of amphidinolides C, C2, and F.

Authors:  Laurent Ferrié; Bruno Figadère
Journal:  Org Lett       Date:  2010-11-05       Impact factor: 6.005

6.  Synthesis of vinyl boronates from aldehydes by a practical boron-Wittig reaction.

Authors:  John R Coombs; Liang Zhang; James P Morken
Journal:  Org Lett       Date:  2015-03-23       Impact factor: 6.005

7.  Synthesis of the C-18-C-34 fragment of amphidinolides C, C2, and C3.

Authors:  J Stephen Clark; Guang Yang; Andrew P Osnowski
Journal:  Org Lett       Date:  2013-03-25       Impact factor: 6.005

8.  Enantioselective iridium-catalyzed carbonyl allylation from the alcohol or aldehyde oxidation level using allyl acetate as an allyl metal surrogate.

Authors:  In Su Kim; Ming-Yu Ngai; Michael J Krische
Journal:  J Am Chem Soc       Date:  2008-04-29       Impact factor: 15.419

9.  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

10.  Directed studies towards the total synthesis of (+)-13-deoxytedanolide: simple and convenient synthesis of the C8-C16 fragment.

Authors:  Sébastien Meiries; Alexandra Bartoli; Mélanie Decostanzi; Jean-Luc Parrain; Laurent Commeiras
Journal:  Org Biomol Chem       Date:  2013-08-07       Impact factor: 3.876
View more
  2 in total

1.  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

Review 2.  The Tetrahydrofuran Motif in Polyketide Marine Drugs.

Authors:  Laura Fernández-Peña; Carlos Díez-Poza; Paula González-Andrés; Asunción Barbero
Journal:  Mar Drugs       Date:  2022-02-03       Impact factor: 5.118
  2 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.