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Literature DB >> 25165502

Complex fragment coupling by crotylation: A powerful tool for polyketide natural product synthesis.

Samuel K Reznik¹, Brian S Marcus¹, James L Leighton¹.

Abstract

The first examples of the use of crotylation as a stereocontrolled complex fragment coupling strategy are described. Asymmetric aldehyde isoprenylation provides access to 2-substituted-1,3-butadienes that may be subjected to highly regio- and stereoselective 1,4 hydrosilylation with trichlorosilane. After complexation with a chiral diamine, the 2-sub-stituted-cis-crotylsilanes may be employed in highly diastereoselective Sc(OTf)3-catalyzed aldehdye crotylation reactions.

Entities: Chemical Disease Gene Species

Year: 2012 PMID： 25165502 PMCID： PMC4142647 DOI： 10.1039/C2SC21325G

Source DB: PubMed Journal: Chem Sci ISSN： 2041-6520 Impact factor: 9.825

21 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. Spongipyran Synthetic Studies. Evolution of a Scalable Total Synthesis of (+)-Spongistatin 1.

Authors: Amos B Smith; Chris Sfouggatakis; Christina A Risatti; Jeffrey B Sperry; Wenyu Zhu; Victoria A Doughty; Takashi Tomioka; Dimitar B Gotchev; Clay S Bennett; Satoshi Sakamoto; Onur Atasoylu; Shohei Shirakami; David Bauer; Makoto Takeuchi; Jyunichi Koyanagi; Yasuharu Sakamoto
Journal: Tetrahedron Date: 2009-09-15 Impact factor: 2.457

3. Brønsted acid-catalyzed allylboration: short and stereodivergent synthesis of all four eupomatilone diastereomers with crystallographic assignments.

Authors: Siu Hong Yu; Michael J Ferguson; Robert McDonald; Dennis G Hall
Journal: J Am Chem Soc Date: 2005-09-21 Impact factor: 15.419

4. The stereocontrolled total synthesis of altohyrtin A/spongistatin 1: fragment couplings, completion of the synthesis, analogue generation and biological evaluation.

Authors: Ian Paterson; David Y-K Chen; Mark J Coster; José L Aceña; Jordi Bach; Debra J Wallace
Journal: Org Biomol Chem Date: 2005-05-24 Impact factor: 3.876

5. Spongipyran Synthetic Studies. Total Synthesis of (+)-Spongistatin 2.

Authors: Amos B Smith; Qiyan Lin; Victoria A Doughty; Linghang Zhuang; Mark D McBriar; Jeffrey K Kerns; Armen M Boldi; Noriaki Murase; William H Moser; Christopher S Brook; Clay S Bennett; Kiyoshi Nakayama; Masao Sobukawa; Robert E Lee Trout
Journal: Tetrahedron Date: 2009-08-15 Impact factor: 2.457

6. Multigram synthesis of the C29-C51 subunit and completion of the total synthesis of altohyrtin C (spongistatin 2).

Authors: Clayton H Heathcock; Mark McLaughlin; Jesus Medina; Jed L Hubbs; Grier A Wallace; Robert Scott; Michele M Claffey; Christopher J Hayes; Gregory R Ott
Journal: J Am Chem Soc Date: 2003-10-22 Impact factor: 15.419

7. Altohyrtins B and C and 5-desacetylaltohyrtin A, potent cytotoxic macrolide congeners of altohyrtin A, from the Okinawan marine sponge Hyrtios altum.

Authors: M Kobayashi; S Aoki; H Sakai; N Kihara; T Sasaki; I Kitagawa
Journal: Chem Pharm Bull (Tokyo) Date: 1993-05 Impact factor: 1.645

8. Total synthesis of (+)-chinensiolide B via tandem allylboration/lactonization.

Authors: Tim G Elford; Dennis G Hall
Journal: J Am Chem Soc Date: 2010-02-10 Impact factor: 15.419

9. Gram-scale synthesis of (+)-spongistatin 1: development of an improved, scalable synthesis of the F-ring subunit, fragment union, and final elaboration.

Authors: Amos B Smith; Takashi Tomioka; Christina A Risatti; Jeffrey B Sperry; Chris Sfouggatakis
Journal: Org Lett Date: 2008-08-28 Impact factor: 6.005

Complex fragment coupling by crotylation: A powerful tool for polyketide natural product synthesis.

2. Spongipyran Synthetic Studies. Evolution of a Scalable Total Synthesis of (+)-Spongistatin 1.

3. Brønsted acid-catalyzed allylboration: short and stereodivergent synthesis of all four eupomatilone diastereomers with crystallographic assignments.

4. The stereocontrolled total synthesis of altohyrtin A/spongistatin 1: fragment couplings, completion of the synthesis, analogue generation and biological evaluation.

5. Spongipyran Synthetic Studies. Total Synthesis of (+)-Spongistatin 2.

6. Multigram synthesis of the C29-C51 subunit and completion of the total synthesis of altohyrtin C (spongistatin 2).

7. Altohyrtins B and C and 5-desacetylaltohyrtin A, potent cytotoxic macrolide congeners of altohyrtin A, from the Okinawan marine sponge Hyrtios altum.

8. Total synthesis of (+)-chinensiolide B via tandem allylboration/lactonization.

9. Gram-scale synthesis of (+)-spongistatin 1: development of an improved, scalable synthesis of the F-ring subunit, fragment union, and final elaboration.

10. Direct and highly regioselective and enantioselective allylation of β-diketones.

1. Exploiting pseudo C2-symmetry for an efficient synthesis of the F-ring of the spongistatins.

2. Toward a more step-economical and scalable synthesis of spongistatin 1 to facilitate cancer drug development efforts.

3. A highly step-economical synthesis of dictyostatin.

4. Beyond the Roche ester: a new approach to polypropionate stereotriad synthesis.

5. Hydroxyl-directed stereoselective diboration of alkenes.

6. Silver-Catalyzed Enantioselective Propargylation Reactions of N-Sulfonylketimines.