Literature DB >> 12583754

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

Karl J Hale1, Mark Frigerio, Soraya Manaviazar.   

Abstract

[reaction: see text] The "Southern Hemisphere" intermediate 2, used by Masamune and co-workers for their asymmetric total synthesis of bryostatin 7 (1), has been synthesized from (E)-1,4-hexadiene (11) by a 24-step pathway that has a longest linear sequence of only 20 steps. This is the shortest synthesis of 2 so far recorded, and moreover, it is fully stereocontrolled.

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Year:  2003        PMID： 12583754     DOI： 10.1021/ol027393m

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


  9 in total

1.  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

2.  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

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 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

6.  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

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

9.  Scalable synthesis of bryostatin 1 and analogs, adjuvant leads against latent HIV.

Authors:  Paul A Wender; Clayton T Hardman; Stephen Ho; Matthew S Jeffreys; Jana K Maclaren; Ryan V Quiroz; Steven M Ryckbosch; Akira J Shimizu; Jack L Sloane; Matthew C Stevens
Journal:  Science       Date:  2017-10-13       Impact factor: 47.728
  9 in total

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