Literature DB >> 15202915

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

Eric A Voight1, Paul A Roethle, Steven D Burke.   

Abstract

An efficient synthesis of Hale and co-workers' C17-C27 bryostatin southern hemisphere intermediate has been accomplished in six steps and 33% overall yield from (R)-2-(benzyloxy)propanal. The synthesis features a one-pot DIBALH/HWE ester homologation as well as a novel acetonide rearrangement/glycal formation cascade.

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Year:  2004        PMID： 15202915     DOI： 10.1021/jo0495081

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


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

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

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.  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

5.  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

6.  Total synthesis of bryostatins: the development of methodology for the atom-economic and stereoselective synthesis of the ring C subunit.

Authors:  Barry M Trost; Alison J Frontier; Oliver R Thiel; Hanbiao Yang; Guangbin Dong
Journal:  Chemistry       Date:  2011-07-26       Impact factor: 5.236

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

8.  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
  8 in total

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