Literature DB >> 16178562

Total synthesis of (-)-SNF4435 C and (+)-SNF4435 D.

Christopher M Beaudry1, Dirk Trauner.   

Abstract

[reaction: see text] A convergent, biomimetic total synthesis of the immunosuppressant polyketides SNF4435 C and D is described. The synthetic pathway features a stereo- and regioselective [3,3]-sigmatropic rearrangement as well as a high-yielding Stille coupling/8pi-6pi electrocyclization cascade.

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Year:  2005        PMID： 16178562     DOI： 10.1021/ol051790q

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


  6 in total

1.  Asymmetric induction in 8π electrocyclizations. Design of a removable chiral auxiliary.

Authors:  Keunsoo Kim; Joseph W Lauher; Kathlyn A Parker
Journal:  Org Lett       Date:  2011-12-06       Impact factor: 6.005

2.  Inspirations, discoveries, and future perspectives in total synthesis.

Authors:  K C Nicolaou
Journal:  J Org Chem       Date:  2009-02-06       Impact factor: 4.354

3.  Terminal substituent effects on the reactivity, thermodynamics, and stereoselectivity of the 8π-6π electrocyclization cascades of 1,3,5,7-tetraenes.

Authors:  Ashay Patel; K N Houk
Journal:  J Org Chem       Date:  2014-11-17       Impact factor: 4.354

4.  No acid required: 4π and 6π electrocyclization reactions of dienyl diketones for the synthesis of cyclopentenones and 2H-Pyrans.

Authors:  Steven D Jacob; Joshua L Brooks; Alison J Frontier
Journal:  J Org Chem       Date:  2014-10-17       Impact factor: 4.354

5.  Bioinspired Asymmetric Total Synthesis of Emeriones A-C.

Authors:  Sven Jänner; Daniel Isak; Yuli Li; Kendall N Houk; Aubry K Miller
Journal:  Angew Chem Int Ed Engl       Date:  2022-06-28       Impact factor: 16.823

6.  Total synthesis of endiandric acid J and beilcyclone A from cyclooctatetraene.

Authors:  Oussama Yahiaoui; Adrian Almass; Thomas Fallon
Journal:  Chem Sci       Date:  2020-07-29       Impact factor: 9.825
  6 in total

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