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Literature DB >> 17404602

Synthetic Studies Toward Bryostatin 1: Preparation of a C(1)-C(16) Fragment by Pyran Annulation.

Gary E Keck¹, Dennie S Welch, Yam B Poudel.

Abstract

An expeditious assembly of a C(1)-C(16) subunit of bryostatin 1 is described. A pyran annulation reaction was utilized to form the B-ring by reaction of a hydroxy-allylsilane with a fully elaborated A-ring subunit. This annulation process proceeded with complete diastereoselectivity and in excellent isolated yield despite the presence of potentially sensitive functionality in the A-ring segment.

Entities: Chemical

Year: 2006 PMID： 17404602 PMCID： PMC1847416 DOI： 10.1016/j.tetlet.2006.09.094

Source DB: PubMed Journal: Tetrahedron Lett ISSN： 0040-4039 Impact factor: 2.415

24 in total

1. New, abridged pathway to Masamune's "southern hemisphere" intermediate for the total synthesis of bryostatin 7.

Authors: Karl J Hale; Mark Frigerio; Soraya Manaviazar
Journal: Org Lett Date: 2003-02-20 Impact factor: 6.005

Review 2. The chemistry and biology of the bryostatin antitumour macrolides.

Authors: Karl J Hale; Marc G Hummersone; Soraya Manaviazar; Mark Frigerio
Journal: Nat Prod Rep Date: 2002-08 Impact factor: 13.423

3. 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

Review 4. New insights into the regulation of protein kinase C and novel phorbol ester receptors.

Authors: D Ron; M G Kazanietz
Journal: FASEB J Date: 1999-10 Impact factor: 5.191

5. The exceptional chelating ability of dimethylaluminum chloride and methylaluminum dichloride. The merged stereochemical impact of alpha- and beta-stereocenters in chelate-controlled carbonyl addition reactions with enolsilane and hydride nucleophiles.

Authors: D A Evans; B D Allison; M G Yang; C E Masse
Journal: J Am Chem Soc Date: 2001-11-07 Impact factor: 15.419

Review 6. Protein kinase C (PKC) family in cancer progression.

Authors: Jussi Koivunen; Vesa Aaltonen; Juha Peltonen
Journal: Cancer Lett Date: 2006-04-08 Impact factor: 8.679

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

Authors: Gary E Keck; Jonathan A Covel; Tobias Schiff; Tao Yu
Journal: Org Lett Date: 2002-04-04 Impact factor: 6.005

8. Therapeutic effects of PKC activators in Alzheimer's disease transgenic mice.

Authors: René Etcheberrigaray; Mathew Tan; Ilse Dewachter; Cuno Kuipéri; Ingrid Van der Auwera; Stefaan Wera; Lixin Qiao; Barry Bank; Thomas J Nelson; Alan P Kozikowski; Fred Van Leuven; Daniel L Alkon
Journal: Proc Natl Acad Sci U S A Date: 2004-07-19 Impact factor: 11.205

9. Concise formal synthesis of the bryostatin southern hemisphere (C17-C27).

Authors: Eric A Voight; Paul A Roethle; Steven D Burke
Journal: J Org Chem Date: 2004-06-25 Impact factor: 4.354

10. Total synthesis of (+/-)-trachyspic acid and determination of the relative configuration.

Authors: Kanako Hirai; Hidenori Ooi; Tomoyuki Esumi; Yoshiharu Iwabuchi; Susumi Hatakeyama
Journal: Org Lett Date: 2003-03-20 Impact factor: 6.005

12 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 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

3. 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

4. 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

5. Convergent assembly of highly potent analogues of bryostatin 1 via pyran annulation: bryostatin look-alikes that mimic phorbol ester function.

Authors: Gary E Keck; Matthew B Kraft; Anh P Truong; Wei Li; Carina C Sanchez; Noemi Kedei; Nancy E Lewin; Peter M Blumberg
Journal: J Am Chem Soc Date: 2008-05-02 Impact factor: 15.419

6. Synthesis and Biological Evaluation of Fluorescent Bryostatin Analogues.

Authors: Thomas J Cummins; Noemi Kedei; Agnes Czikora; Nancy E Lewin; Sharon Kirk; Mark E Petersen; Kevin M McGowan; Jin-Qiu Chen; Xiaoling Luo; Randall C Johnson; Sarangan Ravichandran; Peter M Blumberg; Gary E Keck
Journal: Chembiochem Date: 2018-03-25 Impact factor: 3.164

7. Molecular modeling, total synthesis, and biological evaluations of C9-deoxy bryostatin 1.

Authors: Gary E Keck; Yam B Poudel; Arnab Rudra; Jeffrey C Stephens; Noemi Kedei; Nancy E Lewin; Megan L Peach; Peter M Blumberg
Journal: Angew Chem Int Ed Engl Date: 2010-06-21 Impact factor: 15.336

8. Total synthesis of epothilones B and D: stannane equivalents for beta-keto ester dianions.

Authors: Gary E Keck; Robert L Giles; Victor J Cee; Carrie A Wager; Tao Yu; Matthew B Kraft
Journal: J Org Chem Date: 2008-12-19 Impact factor: 4.354

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. Concise synthesis of the bryostatin A-ring via consecutive C-C bond forming transfer hydrogenations.

Authors: Yu Lu; Michael J Krische
Journal: Org Lett Date: 2009-07-16 Impact factor: 6.005