Literature DB >> 17031426

Synthesis of the DEF-bis-spiroacetal of spirastrellolide A exploiting a double asymmetric dihydroxylation/spiroacetalisation strategy.

Ian Paterson1, Edward A Anderson, Stephen M Dalby, Jong Ho Lim, Philip Maltas, Christian Moessner.   

Abstract

An efficient synthesis of the C(26)-C(40) tricyclic [5,6,6]-bis-spiroacetal segment of the marine macrolide spirastrellolide A has been developed, exploiting a novel double Sharpless asymmetric dihydroxylation/spiroacetalisation sequence.

Entities:  

Year:  2006        PMID： 17031426     DOI： 10.1039/b612697a

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN： 1359-7345            Impact factor:   6.222


  7 in total

1.  INTEGRATED APPROACHES TO THE CONFIGURATIONAL ASSIGNMENT OF MARINE NATURAL PRODUCTS.

Authors:  Tadeusz F Molinski; Brandon I Morinaka
Journal:  Tetrahedron       Date:  2012-11-18       Impact factor: 2.457

Review 2.  The economies of synthesis.

Authors:  Timothy Newhouse; Phil S Baran; Reinhard W Hoffmann
Journal:  Chem Soc Rev       Date:  2009-08-21       Impact factor: 54.564

3.  Spirastrellolide B: construction of the C(26)-C(40) northern hemisphere and a related [5,5,7]-bis-spiroketal analogue.

Authors:  Xiaozhao Wang; Thomas J Paxton; Ningkun Li; Amos B Smith
Journal:  Org Lett       Date:  2012-07-24       Impact factor: 6.005

Review 4.  Challenges and discoveries in the total synthesis of complex polyketide natural products.

Authors:  Ian Paterson; Nelson Yuen Sum Lam
Journal:  J Antibiot (Tokyo)       Date:  2017-10-25       Impact factor: 2.649

5.  Spirastrellolide E: Synthesis of an advanced C(1)-C(24) southern hemisphere.

Authors:  Alexander Sokolsky; Xiaozhao Wang; Amos B Smith
Journal:  Tetrahedron Lett       Date:  2015-06-03       Impact factor: 2.415

6.  Spirastrellolide Studies. Synthesis of the C(1)-C(25) Southern Hemispheres of Spirastrellolides A and B, Exploiting Anion Relay Chemistry.

Authors:  Amos B Smith; Helmars Smits; Dae-Shik Kim
Journal:  Tetrahedron       Date:  2010-08-14       Impact factor: 2.457

7.  Synthesis of a C(1)-C(23) fragment for spirastrellolide E: development of a mechanistic rationale for spiroketalization.

Authors:  Alexander Sokolsky; Martin Cattoen; Amos B Smith
Journal:  Org Lett       Date:  2015-04-06       Impact factor: 6.005
  7 in total

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