Literature DB >> 19055428

Synthesis of C14,15-dihydro-C22,25-epi north unit of cephalostatin 1 via "red-ox" modifications of hecogenin acetate.

Seongmin Lee1, Daniel Jamieson, Philip L Fuchs.   

Abstract

The C14,15-dihydro-C22,25-epi north unit of cephalostatin 1 has been synthesized in 11 operations from commercially available hecogenin acetate via multiple reductions and oxidations. The key transformations include (i) Cr(VI)-catalyzed E-ring opening, (ii) C17 hydroxylation, and (iii) a base-triggered cyclization cascade.

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Year:  2009        PMID： 19055428      PMCID： PMC2859694          DOI： 10.1021/ol802122p

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


  15 in total

1.  A new strategy for the stereoselective introduction of steroid side chain via alpha-alkoxy vinyl cuprates: total synthesis of a highly potent antitumor natural product OSW-1.

Authors:  W Yu; Z Jin
Journal:  J Am Chem Soc       Date:  2001-04-11       Impact factor: 15.419

2.  The first total synthesis of (corrected) ritterazine M.

Authors:  Seongmin Lee; Philip L Fuchs
Journal:  Org Lett       Date:  2002-02-07       Impact factor: 6.005

3.  Chemospecific chromium[VI] catalyzed oxidation of C-H bonds at -40 degrees C1.

Authors:  Seongmin Lee; P L Fuchs
Journal:  J Am Chem Soc       Date:  2002-11-27       Impact factor: 15.419

4.  Synthesis of Bis-18,18'-desmethyl Ritterazine N.

Authors:  Douglass F Taber; Jean-Michel Joerger
Journal:  J Org Chem       Date:  2008-05-08       Impact factor: 4.354

5.  Synthesis of symmetrical and unsymmetrical pyrazines.

Authors:  Douglass F Taber; Peter W DeMatteo; Karen V Taluskie
Journal:  J Org Chem       Date:  2007-01-24       Impact factor: 4.354

6.  A convenient synthesis of C-22 and C-25 stereoisomers of cephalostatin north 1 side chain from spirostan sapogenins.

Authors:  Carmen Betancor; Raimundo Freire; Inés Pérez-Martín; Thierry Prangé; Ernesto Suárez
Journal:  Org Lett       Date:  2002-04-18       Impact factor: 6.005

7.  Isolation of 13 New Ritterazines from the Tunicate Ritterella tokioka and Chemical Transformation of Ritterazine B(1).

Authors:  Seketsu Fukuzawa; Shigeki Matsunaga; Nobuhiro Fusetani
Journal:  J Org Chem       Date:  1997-06-27       Impact factor: 4.354

8.  Dyotropic rearrangement facilitated proximal functionalization and oxidative removal of angular methyl groups: efficient syntheses of 23'-deoxy cephalostatin 1 analogues.

Authors:  Wei Li; Thomas G LaCour; P L Fuchs
Journal:  J Am Chem Soc       Date:  2002-05-01       Impact factor: 15.419

9.  Syntheses of the eastern halves of ritterazines B, F, G, and H, leading to reassignment of the 5,5-spiroketal stereochemistry of ritterazines B and F.

Authors:  Scott T Phillips; Matthew D Shair
Journal:  J Am Chem Soc       Date:  2007-05-01       Impact factor: 15.419

10.  Computationally guided organometallic chemistry: preparation of the heptacyclic pyrazine core of ritterazine N.

Authors:  Douglass F Taber; Karen V Taluskie
Journal:  J Org Chem       Date:  2006-03-31       Impact factor: 4.354
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  3 in total

1.  The cephalostatins. 22. synthesis of bis-steroidal pyrazine pyrones (1).

Authors:  George R Pettit; Bryan R Moser; Ricardo F Mendonça; John C Knight; Fiona Hogan
Journal:  J Nat Prod       Date:  2012-05-18       Impact factor: 4.050

2.  The cephalostatins. 21. Synthesis of bis-steroidal pyrazine rhamnosides (1).

Authors:  George R Pettit; Ricardo F Mendonça; John C Knight; Robin K Pettit
Journal:  J Nat Prod       Date:  2011-09-07       Impact factor: 4.050

3.  A convergent total synthesis of the potent cephalostatin/ritterazine hybrid -25-epi ritterostatin GN1N.

Authors:  Ananda Kumar Kanduluru; Prabal Banerjee; John A Beutler; Philip L Fuchs
Journal:  J Org Chem       Date:  2013-08-29       Impact factor: 4.354
  3 in total

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