Literature DB >> 16381554

Amphidinolide B: asymmetric synthesis of a C7-C20 synthon.

Apsara Gopalarathnam1, Scott G Nelson.   

Abstract

[reaction: see text] An asymmetric synthesis of a C(7)-C(20) synthon of amphidinolide B is described. The synthesis entails the construction of C(7)-C(13) and C(14)-C(20) fragments and makes extensive use of catalytic asymmetric bond constructions to establish the requisite stereochemical relationships. Fragment coupling proceeds by Suzuki cross-coupling and installs the trisubstituted diene unit that is among amphidinolide B's defining structural features.

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Year:  2006        PMID： 16381554     DOI： 10.1021/ol051861l

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


  11 in total

1.  Suzuki-Miyaura cross-coupling of 3-pyridyl triflates with 1-alkenyl-2-pinacol boronates.

Authors:  James R Vyvyan; Jennifer A Dell Née Meyer; Toby J Ligon; Kelsey K Motanic; Hayley S Wall
Journal:  Synthesis (Stuttg)       Date:  2010-11       Impact factor: 3.157

2.  Synthesis of the C3-C18 fragment of amphidinolides G and H.

Authors:  Andreas F Petri; John S Schneekloth; Amit K Mandal; Craig M Crews
Journal:  Org Lett       Date:  2007-07-07       Impact factor: 6.005

3.  Preparation and wittig reactions of organotrifluoroborato phosphonium ylides.

Authors:  Gary A Molander; Jungyeob Ham; Belgin Canturk
Journal:  Org Lett       Date:  2007-02-06       Impact factor: 6.005

4.  Total synthesis of cytotoxic macrolide amphidinolide B1 and the proposed structure of amphidinolide B2.

Authors:  Liang Lu; Wei Zhang; Rich G Carter
Journal:  J Am Chem Soc       Date:  2008-05-20       Impact factor: 15.419

5.  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

6.  Iterative Cross-Couplng with MIDA Boronates: Towards a General Platform for Small Molecule Synthesis.

Authors:  Eric P Gillis; Martin D Burke
Journal:  Aldrichimica Acta       Date:  2009       Impact factor: 3.667

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.  Multistep synthesis of complex boronic acids from simple MIDA boronates.

Authors:  Eric P Gillis; Martin D Burke
Journal:  J Am Chem Soc       Date:  2008-10-07       Impact factor: 15.419

9.  Design and synthesis of novel pinacolylboronate containing combretastatin 'antimitotic agent' analogues.

Authors:  Bhaskar C Das; Sakkarapalayam M Mahalingam; Todd Evans
Journal:  Tetrahedron Lett       Date:  2009-06-24       Impact factor: 2.415

Review 10.  Synthetic applications of chiral unsaturated epoxy alcohols prepared by sharpless asymmetric epoxidation.

Authors:  Antoni Riera; María Moreno
Journal:  Molecules       Date:  2010-02-23       Impact factor: 4.411
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