Literature DB >> 15584723

The total synthesis of (-)-SNF4435 C and (+)-SNF4435 D.

Kathlyn A Parker1, Yeon-Hee Lim.   

Abstract

The size and positioning of substituents on a tetraene, along with the Woodward-Hoffmann rules, control the relative stereochemistry at the four adjacent chiral centers that are generated in the 8pi/6pi electrocyclization cascade. A biomimetic synthesis of (-)-SNF4435 C and (+)-SNF4435 D exploits these steric effects and allows confirmation of the predicted absolute stereochemistry of the natural products.

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Year:  2004        PMID: 15584723     DOI: 10.1021/ja044733l

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  10 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.  Total synthesis of the potent androgen receptor antagonist (-)-arabilin: a strategic, biomimetic [1,7]-hydrogen shift.

Authors:  Hee Nam Lim; Kathlyn A Parker
Journal:  J Am Chem Soc       Date:  2011-11-29       Impact factor: 15.419

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

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

4.  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

5.  Total synthesis of clostrubin.

Authors:  Ming Yang; Jian Li; Ang Li
Journal:  Nat Commun       Date:  2015-03-11       Impact factor: 14.919

6.  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

Review 7.  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

8.  The synthesis of some novel stilbene dimers incorporating diamide tethers: studies in single electron transfer oxidation (FeCl3).

Authors:  Maryam Sadat Alehashem; Azhar Ariffin; Amjad Ayad Qatran Al-Khdhairawi; Noel F Thomas
Journal:  RSC Adv       Date:  2018-01-11       Impact factor: 3.361

9.  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

10.  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

  10 in total

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