Literature DB >> 19873984

Symmetric macrocycles by a Prins dimerization and macrocyclization strategy.

Michael R Gesinski1, Kwanruthai Tadpetch, Scott D Rychnovsky.   

Abstract

A tandem dimerization/macrocyclization reaction utilizing the Prins cyclization has been developed. This reaction develops molecular complexity through the formation of highly substituted dimeric tetrahydropyran macrocycles. Mild conditions utilizing rhenium(VII) catalysts were explored for aromatic substrates, while harsher Lewis acidic conditions were used for aliphatic substrates. Both aldehydes and acetals are shown to be viable substrates for this reaction.

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Year:  2009        PMID： 19873984      PMCID： PMC2905591          DOI： 10.1021/ol9022062

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


  26 in total

1.  The first and highly enantioselective crotylation of aldehydes via an allyl-transfer reaction from a chiral crotyl-donor.

Authors:  J Nokami; M Ohga; H Nakamoto; T Matsubara; I Hussain; K Kataoka
Journal:  J Am Chem Soc       Date:  2001-09-19       Impact factor: 15.419

2.  Highly enantioselective Alk-2-enylation of aldehydes through an allyl-transfer reaction.

Authors:  Junzo Nokami; Kenta Nomiyama; Seiji Matsuda; Nobuyuki Imai; Kazuhide Kataoka
Journal:  Angew Chem Int Ed Engl       Date:  2003-03-17       Impact factor: 15.336

3.  Clavosolides A and B, dimeric macrolides from the Philippines sponge Myriastra clavosa.

Authors:  M Rama Rao; D John Faulkner
Journal:  J Nat Prod       Date:  2002-03       Impact factor: 4.050

4.  Total synthesis of (-)-cylindrocyclophanes A and F exploiting the reversible nature of the olefin cross metathesis reaction.

Authors:  A B Smith; C M Adams; S A Kozmin; D V Paone
Journal:  J Am Chem Soc       Date:  2001-06-27       Impact factor: 15.419

5.  Sequential acyl halide-aldehyde cyclocondensation and enzymatic resolution as a route to enantiomerically enriched beta-lactones.

Authors:  S G Nelson; K L Spencer
Journal:  J Org Chem       Date:  2000-02-25       Impact factor: 4.354

6.  Total synthesis of cryptophycin-24 (Arenastatin A) amenable to structural modifications in the C16 side chain.

Authors:  M Eggen; C J Mossman; S B Buck; S K Nair; L Bhat; S M Ali; E A Reiff; T C Boge; G I Georg
Journal:  J Org Chem       Date:  2000-11-17       Impact factor: 4.354

7.  Rhenium(VII) catalysis of Prins cyclization reactions.

Authors:  Kwanruthai Tadpetch; Scott D Rychnovsky
Journal:  Org Lett       Date:  2008-09-25       Impact factor: 6.005

8.  Stereoselective synthesis of 4-hydroxy-2,3,6-trisubstituted tetrahydropyrans.

Authors:  Conor St J Barry; Stuart R Crosby; John R Harding; Rachael A Hughes; Clare D King; Gregory D Parker; Christine L Willis
Journal:  Org Lett       Date:  2003-07-10       Impact factor: 6.005

9.  Total synthesis and structural revision of the marine macrolide neopeltolide.

Authors:  Daniel W Custar; Thomas P Zabawa; Karl A Scheidt
Journal:  J Am Chem Soc       Date:  2008-01-23       Impact factor: 15.419

10.  Stereochemical diversity through cyclodimerization: synthesis of polyketide-like macrodiolides.

Authors:  Qibin Su; Aaron B Beeler; Emil Lobkovsky; John A Porco; James S Panek
Journal:  Org Lett       Date:  2003-06-12       Impact factor: 6.005
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  10 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.  Enantioselective synthesis of (-)-exiguolide by iterative stereoselective dioxinone-directed Prins cyclizations.

Authors:  Erika A Crane; Thomas P Zabawa; Rebecca L Farmer; Karl A Scheidt
Journal:  Angew Chem Int Ed Engl       Date:  2011-09-19       Impact factor: 15.336

4.  Lead Diversification through a Prins-Driven Macrocyclization Strategy: Application to C13-Diversified Bryostatin Analogues.

Authors:  Paul A Wender; Kelvin L Billingsley
Journal:  Synthesis (Stuttg)       Date:  2013       Impact factor: 3.157

5.  Total synthesis of bryostatin 9.

Authors:  Paul A Wender; Adam J Schrier
Journal:  J Am Chem Soc       Date:  2011-05-27       Impact factor: 15.419

6.  Regio- and stereocontrol in rhenium-catalyzed transposition of allylic alcohols.

Authors:  Aaron T Herrmann; Tatsuo Saito; Craig E Stivala; Janine Tom; Armen Zakarian
Journal:  J Am Chem Soc       Date:  2010-05-05       Impact factor: 15.419

7.  Atom economical, one-pot, three-reaction cascade to novel tricyclic 2,4-dihydro-1H-benzo[f]isochromenes.

Authors:  Robert J Hinkle; Shane E Lewis
Journal:  Org Lett       Date:  2013-08-01       Impact factor: 6.005

Review 8.  Prins-type macrocyclizations as an efficient ring-closing strategy in natural product synthesis.

Authors:  Erika A Crane; Karl A Scheidt
Journal:  Angew Chem Int Ed Engl       Date:  2010-11-02       Impact factor: 15.336

9.  Mechanistic and computational studies of exocyclic stereocontrol in the synthesis of bryostatin-like cis-2,6-disubstituted 4-alkylidenetetrahydropyrans by Prins cyclization.

Authors:  Yasuyuki Ogawa; Phillip P Painter; Dean J Tantillo; Paul A Wender
Journal:  J Org Chem       Date:  2012-11-07       Impact factor: 4.354

10.  Boron carboxylate catalysis of homoallylboration.

Authors:  Gabrielle J Dugas; Yu-hong Lam; K N Houk; Isaac J Krauss
Journal:  J Org Chem       Date:  2014-04-24       Impact factor: 4.354
  10 in total

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