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Literature DB >> 15901156

Synthetic studies on the bryostatins: preparation of a truncated BC-ring intermediate by pyran annulation.

Abstract

[reaction: see text]. A synthesis of a potential BC-ring subunit (C9-C27) for bryostatin 1, a remarkably potent anticancer agent, has been developed in 16 steps and 18% overall yield. The key features of this route include a BITIP-catalyzed asymmetric allylation reaction, chelation-controlled allylations, a hydroformylation reaction, and a pyran annulation reaction.

Entities: Chemical

Mesh：

Substances：

Year: 2005 PMID： 15901156 PMCID： PMC1480406 DOI： 10.1021/ol050511w

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

11 in total

1. Total Synthesis of Bryostatin 3 This work was supported by the Ministry of Education, Science, Sports, and Culture (Japan). K.O. is grateful to JSPS for a predoctoral fellowship. The authors thank Dr. G. N. Chmurny (NIH) for providing them with (1)H and (13)C NMR spectra of bryostatin 3 and for helpful discussions.

Authors:
Journal: Angew Chem Int Ed Engl Date: 2000-07-03 Impact factor: 15.336

2. 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

3. The practical synthesis of a novel and highly potent analogue of bryostatin.

Authors: Paul A Wender; Jeremy L Baryza; Chad E Bennett; F Christopher Bi; Stacey E Brenner; Michael O Clarke; Joshua C Horan; Cindy Kan; Emmanuel Lacôte; Blaise Lippa; Peter G Nell; Tim M Turner
Journal: J Am Chem Soc Date: 2002-11-20 Impact factor: 15.419

Review 4. 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

5. Synthesis of the bryostatin 1 northern hemisphere (C1-C16) via desymmetrization by ketalization/ring-closing metathesis.

Authors: Eric A Voight; Hassan Seradj; Paul A Roethle; Steven D Burke
Journal: Org Lett Date: 2004-10-28 Impact factor: 6.005

6. Synthetic studies on the bryostatins: synthetic routes to analogues containing the tricyclic macrolactone core.

Authors: Gary E Keck; Anh P Truong
Journal: Org Lett Date: 2005-05-26 Impact factor: 6.005

7. Enantio- and diastereoselective additions to aldehydes using the bifunctional reagent 2-(chloromethyl)-3-(tributylstannyl)propene: application to a synthesis of the C16-C27 segment of bryostatin 1.

Authors: Gary E Keck; Tao Yu; Mark D McLaws
Journal: J Org Chem Date: 2005-04-01 Impact factor: 4.354

Review 8. Chemistry and clinical biology of the bryostatins.

Authors: R Mutter; M Wills
Journal: Bioorg Med Chem Date: 2000-08 Impact factor: 3.641

9. 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

10. 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

18 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. 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

4. 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

5. 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

6. 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

7. 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

8. Deletion of the C26 Methyl Substituent from the Bryostatin Analogue Merle 23 Has Negligible Impact on Its Biological Profile and Potency.

Authors: Xiguang Zhao; Noemi Kedei; Alexandra Michalowski; Nancy E Lewin; Gary E Keck; Peter M Blumberg
Journal: Chembiochem Date: 2018-04-27 Impact factor: 3.164

9. Synthetic studies on the bryostatins: synthetic routes to analogues containing the tricyclic macrolactone core.

Authors: Gary E Keck; Anh P Truong
Journal: Org Lett Date: 2005-05-26 Impact factor: 6.005

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

Authors: Gary E Keck; Dennie S Welch; Yam B Poudel
Journal: Tetrahedron Lett Date: 2006-11-20 Impact factor: 2.415