Literature DB >> 11922815

Pyran annulation: asymmetric synthesis of 2,6-disubstituted-4-methylene tetrahydropyrans.

Gary E Keck1, Jonathan A Covel, Tobias Schiff, Tao Yu.   

Abstract

[reaction: see text] A reaction process for the asymmetric construction of a variety of cis or trans disubstituted pyrans is described. This sequences allows for the asymmetric convergent union of two aldehydes with silyl-stannane reagent 1 in a two-step process: catalytic asymmetric allylation of the first aldehyde using 1 with a BITIP catalyst, followed by reaction of the alcohol so obtained with a second aldehyde and TMSOTf.

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Year:  2002        PMID： 11922815      PMCID： PMC1480410          DOI： 10.1021/ol025645d

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


  13 in total

1.  Efficient stereochemical relay en route to leucascandrolide A.

Authors:  S A Kozmin
Journal:  Org Lett       Date:  2001-03-08       Impact factor: 6.005

2.  An oxidative prins cyclization methodology.

Authors:  C Chen; P S Mariano
Journal:  J Org Chem       Date:  2000-05-19       Impact factor: 4.354

3.  Total Synthesis of Bryostatin 3 This work was supported by the Ministry of Education, Science, Sports, and Culture (Japan). K.O. is grateful to JSPS for a predoctoral fellowship. The authors thank Dr. G. N. Chmurny (NIH) for providing them with (1)H and (13)C NMR spectra of bryostatin 3 and for helpful discussions.

Authors: 
Journal:  Angew Chem Int Ed Engl       Date:  2000-07-03       Impact factor: 15.336

4.  Stereoselective Cyclization of Highly Enantioenriched Allylsilanes with Aldehydes via Acetal Formation: New Asymmetric Access to Tetrahydropyrans and Piperidines.

Authors:  Michinori Suginome; Taisuke Iwanami; Yoshihiko Ito
Journal:  J Org Chem       Date:  1998-09-04       Impact factor: 4.354

5.  Total synthesis of (+)-phorboxazole A.

Authors:  A B Smith; P R Verhoest; K P Minbiole; M Schelhaas
Journal:  J Am Chem Soc       Date:  2001-05-23       Impact factor: 15.419

6.  Stereocontrolled Preparation of Spirocyclic Ethers by Intramolecular Trapping of Oxonium Ions with Allylsilanes.

Authors:  Leo A. Paquette; Jinsung Tae
Journal:  J Org Chem       Date:  1996-11-01       Impact factor: 4.354

7.  Phorboxazole synthetic studies. 1. Construction of a C(3-19) subtarget exploiting an extension of the Petasis-Ferrier rearrangement.

Authors:  A B Smith; P R Verhoest; K P Minbiole; J J Lim
Journal:  Org Lett       Date:  1999-09-23       Impact factor: 6.005

Review 8.  The rational design of potential chemotherapeutic agents: synthesis of bryostatin analogues.

Authors:  P A Wender; K W Hinkle; M F Koehler; B Lippa
Journal:  Med Res Rev       Date:  1999-09       Impact factor: 12.944

9.  Stereoselectivity and regioselectivity in the segment-coupling Prins cyclization.

Authors:  J J Jaber; K Mitsui; S D Rychnovsky
Journal:  J Org Chem       Date:  2001-06-29       Impact factor: 4.354

10.  The design, computer modeling, solution structure, and biological evaluation of synthetic analogs of bryostatin 1.

Authors:  P A Wender; J DeBrabander; P G Harran; J M Jimenez; M F Koehler; B Lippa; C M Park; C Siedenbiedel; G R Pettit
Journal:  Proc Natl Acad Sci U S A       Date:  1998-06-09       Impact factor: 11.205
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  32 in total

1.  Translating Nature's Library: The Bryostatins and Function-Oriented Synthesis.

Authors:  Paul A Wender; Brian A Loy; Adam J Schrier
Journal:  Isr J Chem       Date:  2011-03-24       Impact factor: 3.333

2.  Total synthesis of the cyanolide A aglycon.

Authors:  Michael R Gesinski; Scott D Rychnovsky
Journal:  J Am Chem Soc       Date:  2011-06-08       Impact factor: 15.419

3.  Total synthesis of bryostatin 1.

Authors:  Gary E Keck; Yam B Poudel; Thomas J Cummins; Arnab Rudra; Jonathan A Covel
Journal:  J Am Chem Soc       Date:  2010-12-22       Impact factor: 15.419

4.  Synthesis of Functionalized 4-Methylenetetrahydropyrans by Oxidative Activation of Cinnamyl or Benzyl Ethers.

Authors:  Arun K Ghosh; Xu Cheng
Journal:  Tetrahedron Lett       Date:  2012-05-16       Impact factor: 2.415

5.  Synthetic studies on the bryostatins: preparation of a truncated BC-ring intermediate by pyran annulation.

Authors:  Gary E Keck; Anh P Truong
Journal:  Org Lett       Date:  2005-05-26       Impact factor: 6.005

6.  Synthetic studies toward the bryostatins: a substrate-controlled approach to the A-ring.

Authors:  Gary E Keck; Dennie S Welch; Paige K Vivian
Journal:  Org Lett       Date:  2006-08-17       Impact factor: 6.005

7.  A catalytic asymmetric vinylogous Mukaiyama aldol reaction.

Authors:  Lars V Heumann; Gary E Keck
Journal:  Org Lett       Date:  2007-09-21       Impact factor: 6.005

8.  A new construction of 2-alkoxypyrans by an acylation-reductive cyclization sequence.

Authors:  Lars V Heumann; Gary E Keck
Journal:  Org Lett       Date:  2007-04-12       Impact factor: 6.005

9.  Substitution on the A-ring confers to bryopyran analogues the unique biological activity characteristic of bryostatins and distinct from that of the phorbol esters.

Authors:  Gary E Keck; Yam B Poudel; Dennie S Welch; Matthew B Kraft; Anh P Truong; Jeffrey C Stephens; Noemi Kedei; Nancy E Lewin; Peter M Blumberg
Journal:  Org Lett       Date:  2009-02-05       Impact factor: 6.005

10.  A tandem isomerization/prins strategy: iridium(III)/Brønsted acid cooperative catalysis.

Authors:  Vince M Lombardo; Christopher D Thomas; Karl A Scheidt
Journal:  Angew Chem Int Ed Engl       Date:  2013-11-11       Impact factor: 15.336
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