Literature DB >> 22146007

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

Keunsoo Kim1, Joseph W Lauher, Kathlyn A Parker.   

Abstract

The pseudo C(2) symmetric trans diphenyl oxazoline group acts as an effective chiral auxiliary in the 8π, 6π tandem electrocyclization of a substituted tetraene 1-carboxylic acid. Assignment of absolute stereochemistry to the [4.2.0] bicyclooctadiene product supports a model in which both s-cis and s-trans conformations favor the transition states with the same helical twist. This assignment prefaces the development of analogs of SNF4435 C and D. These natural products demonstrate activity as androgen receptor antagonists and as multidrug resistance (mdr) reversal agents.
© 2011 American Chemical Society

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Year:  2011        PMID： 22146007      PMCID： PMC3320032          DOI： 10.1021/ol202932x

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


  11 in total

1.  "Endo" and "exo" bicyclo[4.2.0]-octadiene isomers from the electrocyclization of fully substituted tetraene models for SNF 4435C and D. control of stereochemistry by choice of a functionalized substituent.

Authors:  Kathlyn A Parker; Yeon-Hee Lim
Journal:  Org Lett       Date:  2004-01-22       Impact factor: 6.005

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

Authors:  Christopher M Beaudry; Dirk Trauner
Journal:  Org Lett       Date:  2005-09-29       Impact factor: 6.005

3.  Mining the tetraene manifold: total synthesis of complex pyrones from Placobranchus ocellatus.

Authors:  Aubry K Miller; Dirk Trauner
Journal:  Angew Chem Int Ed Engl       Date:  2005-07-18       Impact factor: 15.336

4.  Cleavable chiral auxiliaries in 8pi (8pi, 6pi) electrocyclizations.

Authors:  Kathlyn A Parker; Zhongyu Wang
Journal:  Org Lett       Date:  2006-08-03       Impact factor: 6.005

5.  The total synthesis of spectinabilin and its biomimetic conversion to SNF4435C and SNF4435D.

Authors:  Mikkel F Jacobsen; John E Moses; Robert M Adlington; Jack E Baldwin
Journal:  Org Lett       Date:  2005-06-09       Impact factor: 6.005

Review 6.  Asymmetric electrocyclic reactions.

Authors:  Sam Thompson; Anthony G Coyne; Peter C Knipe; Martin D Smith
Journal:  Chem Soc Rev       Date:  2011-05-12       Impact factor: 54.564

7.  Isolation and structure elucidation of a novel androgen antagonist, arabilin, produced by Streptomyces sp. MK756-CF1.

Authors:  Tatsuro Kawamura; Takahiro Fujimaki; Natsuki Hamanaka; Kentaro Torii; Hiroki Kobayashi; Yoshikazu Takahashi; Masayuki Igarashi; Naoko Kinoshita; Yoshio Nishimura; Etsu Tashiro; Masaya Imoto
Journal:  J Antibiot (Tokyo)       Date:  2010-08-25       Impact factor: 2.649

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

Authors:  Kathlyn A Parker; Yeon-Hee Lim
Journal:  J Am Chem Soc       Date:  2004-12-15       Impact factor: 15.419

9.  Biomimetic synthesis of elysiapyrones A and B.

Authors:  Jennifer E Barbarow; Aubry K Miller; Dirk Trauner
Journal:  Org Lett       Date:  2005-07-07       Impact factor: 6.005

10.  Biomimetic synthesis of the shimalactones.

Authors:  Vladimir Sofiyev; Gabriel Navarro; Dirk Trauner
Journal:  Org Lett       Date:  2007-12-12       Impact factor: 6.005
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  3 in total

1.  Total synthesis of kingianin A.

Authors:  Hee Nam Lim; Kathlyn A Parker
Journal:  Org Lett       Date:  2012-12-28       Impact factor: 6.005

2.  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

3.  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
  3 in total

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