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Literature DB >> 22260643

Studies toward the synthesis of spirolide C: exploration into the formation of the 23-membered all-carbon macrocyclic framework.

Craig E Stivala¹, Zhenhua Gu, Lindsay L Smith, Armen Zakarian.

Abstract

The synthesis of two complex subunits en route to spirolide C is described. A key alkyllithium addition to an aldehyde joins the fragments, which are advanced in order to investigate a ring-closing metathesis to form the 23-membered all-carbon macrocyclic framework.

Entities: Chemical Disease Species

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Year: 2012 PMID： 22260643 PMCID： PMC3366693 DOI： 10.1021/ol203342e

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

26 in total

1. The Spongistatins: Architecturally Complex Natural Products-Part One: A Formal Synthesis of (+)-Spongistatin 1 by Construction of an Advanced ABCD Fragment Financial support was provided by the National Institutes of Health (National Cancer Institute) through Grant CA-70329, NIH Postdoctoral Fellowships to A.M.B. and W.H.M., a Japan Society for Promotion of Science Fellowship to N.M., and a Royal Society Fulbright Fellowship to V.A.D. We also thank the Daiichi Pharmaceutical Co., Ltd, and the Tanabe Seiyaku Co., Ltd for financial support. Finally we thank Dr. George T. Furst, Dr. Patrick J. Carroll, Dr. Rakesh Kohli, and Mr John Dykins of the University of Pennsylvania Spectroscopic Service Center for assistance in securing and interpreting high-field NMR spectra, X-ray crystal structures, and mass spectra.

Authors: Amos B. Smith III; Victoria A. Doughty; Qiyan Lin; Linghang Zhuang; Mark D. McBriar; Armen M. Boldi; William H. Moser; Noriaki Murase; Kiyoshi Nakayama; Masao Sobukawa
Journal: Angew Chem Int Ed Engl Date: 2001-01-05 Impact factor: 15.336

2. Characterization of spirolides a, c, and 13-desmethyl c, new marine toxins isolated from toxic plankton and contaminated shellfish.

Authors: T Hu; I W Burton; A D Cembella; J M Curtis; M A Quilliam; J A Walter; J L Wright
Journal: J Nat Prod Date: 2001-03 Impact factor: 4.050

3. Acyclic stereocontrol in the Ireland-Claisen rearrangement of alpha-branched esters.

Authors: Ying-chuan Qin; Craig E Stivala; Armen Zakarian
Journal: Angew Chem Int Ed Engl Date: 2007 Impact factor: 15.336

4. Synthesis of a C(1)-C(14)-containing fragment of callipeltoside A.

Authors: T R Hoye; H Zhao
Journal: Org Lett Date: 1999-07-15 Impact factor: 6.005

5. Synthesis of the bis-spiroacetal moiety of spirolides B and D.

Authors: Kai Meilert; Margaret A Brimble
Journal: Org Lett Date: 2005-08-04 Impact factor: 6.005

6. Total synthesis of pinnatoxins A and G and revision of the mode of action of pinnatoxin A.

Authors: Romulo Araoz; Denis Servent; Jordi Molgó; Bogdan I Iorga; Carole Fruchart-Gaillard; Evelyne Benoit; Zhenhua Gu; Craig Stivala; Armen Zakarian
Journal: J Am Chem Soc Date: 2011-06-17 Impact factor: 15.419

7. Prevention of undesirable isomerization during olefin metathesis.

Authors: Soon Hyeok Hong; Daniel P Sanders; Choon Woo Lee; Robert H Grubbs
Journal: J Am Chem Soc Date: 2005-12-14 Impact factor: 15.419

8. Synthesis of the C10-C22 bis-spiroacetal domain of spirolides B and D via iterative oxidative radical cyclization.

Authors: Daniel P Furkert; Margaret A Brimble
Journal: Org Lett Date: 2002-10-17 Impact factor: 6.005

9. Structural determinants in phycotoxins and AChBP conferring high affinity binding and nicotinic AChR antagonism.

Authors: Yves Bourne; Zoran Radic; Rómulo Aráoz; Todd T Talley; Evelyne Benoit; Denis Servent; Palmer Taylor; Jordi Molgó; Pascale Marchot
Journal: Proc Natl Acad Sci U S A Date: 2010-03-11 Impact factor: 11.205

10. Neural injury biomarkers of novel shellfish toxins, spirolides: a pilot study using immunochemical and transcriptional analysis.

Authors: Santokh Gill; Meghan Murphy; Joann Clausen; Don Richard; Michael Quilliam; Shawna MacKinnon; Patricia LaBlanc; Rudi Mueller; Olga Pulido
Journal: Neurotoxicology Date: 2003-08 Impact factor: 4.294

8 in total

Review 1. Synthesis and biology of cyclic imine toxins, an emerging class of potent, globally distributed marine toxins.

Authors: Craig E Stivala; Evelyne Benoit; Rómulo Aráoz; Denis Servent; Alexei Novikov; Jordi Molgó; Armen Zakarian
Journal: Nat Prod Rep Date: 2015-03 Impact factor: 13.423

2. Asymmetric alcohol C-H allylation and syn-crotylation: C9-C20 of tetrafibricin.

Authors: Takahiko Itoh; T Patrick Montgomery; Antonio Recio; Michael J Krische
Journal: Org Lett Date: 2014-01-14 Impact factor: 6.005

3. Evolution of a Unified Strategy for Complex Sesterterpenoids: Progress toward Astellatol and the Total Synthesis of (-)-Nitidasin.

Authors: Daniel T Hog; Florian M E Huber; Gonzalo Jiménez-Osés; Peter Mayer; Kendall N Houk; Dirk Trauner
Journal: Chemistry Date: 2015-08-20 Impact factor: 5.236