Literature DB >> 30393410

An enantioselective synthesis of the C1-C9 segment of antitumor macrolide peloruside A.

Arun K Ghosh1, Jae-Hun Kim1.   

Abstract

A stereocontrolled synthesis of the C1-C9 segment of the marine natural product peloruside A is described. The key steps involve Sharpless's catalytic asymmetric dihydroxylation reaction, a chelation-controlled reduction of chiral β-alkoxy ketones to elaborate the syn-1,3-diol functionality and a ring-closing olefin metathesis of a homoallylic alcohol-derived acrylate ester to form an α,β-unsaturated δ-lactone.

Entities:  

Year:  2003        PMID： 30393410      PMCID： PMC6214207          DOI： 10.1016/S0040-4039(03)00744-5

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN： 0040-4039            Impact factor:   2.415


  10 in total

1.  Chelation-controlled reduction: stereoselective formation of syn-1,3-diols and synthesis of compactin and mevinolin lactone.

Authors:  Arun K Ghosh; Hui Lei
Journal:  J Org Chem       Date:  2002-12-13       Impact factor: 4.354

2.  Asymmetric dihydroxylation route to a dipeptide isostere of a protease inhibitor: enantioselective synthesis of the core unit of ritonavir.

Authors:  Arun K Ghosh; Dongwoo Shin; Packiarajan Mathivanan
Journal:  Chem Commun (Camb)       Date:  1999       Impact factor: 6.222

3.  Potent HIV-1 Protease Inhibitors: Stereoselective Synthesis of a Dipeptide Mimic.

Authors:  Arun K Ghosh; Sean P McKee; Wayne J Thompson; Paul L Darke; Joan C Zugay
Journal:  J Org Chem       Date:  1993-02       Impact factor: 4.354

4.  Total synthesis of microtubule-stabilizing agent (-)-laulimalide.

Authors:  A K Ghosh; Y Wang; J T Kim
Journal:  J Org Chem       Date:  2001-12-28       Impact factor: 4.354

5.  Peloruside A: a potent cytotoxic macrolide isolated from the new zealand marine sponge Mycale sp.

Authors:  L M West; P T Northcote; C N Battershill
Journal:  J Org Chem       Date:  2000-01-28       Impact factor: 4.354

6.  Toward the synthesis of peloruside a: fragment synthesis and coupling studies.

Authors:  Ian Paterson; M Emilia Di Francesco; Toralf Kühn
Journal:  Org Lett       Date:  2003-02-20       Impact factor: 6.005

7.  The novel cytotoxic sponge metabolite peloruside A, structurally similar to bryostatin-1, has unique bioactivity independent of protein kinase C.

Authors:  K A Hood; B T Bäckström; L M West; P T Northcote; M V Berridge; J H Miller
Journal:  Anticancer Drug Des       Date:  2001 Apr-Jun

8.  Epothilones, a new class of microtubule-stabilizing agents with a taxol-like mechanism of action.

Authors:  D M Bollag; P A McQueney; J Zhu; O Hensens; L Koupal; J Liesch; M Goetz; E Lazarides; C M Woods
Journal:  Cancer Res       Date:  1995-06-01       Impact factor: 12.701

9.  The microtubule stabilizing agent laulimalide does not bind in the taxoid site, kills cells resistant to paclitaxel and epothilones, and may not require its epoxide moiety for activity.

Authors:  Donald E Pryor; Aurora O'Brate; Geoffrey Bilcer; J Fernando Díaz; Yuefang Wang; Yong Wang; Mikio Kabaki; M Katherine Jung; José M Andreu; Arun K Ghosh; Paraskevi Giannakakou; Ernest Hamel
Journal:  Biochemistry       Date:  2002-07-23       Impact factor: 3.162

10.  Peloruside A, a novel antimitotic agent with paclitaxel-like microtubule- stabilizing activity.

Authors:  Kylie A Hood; Lyndon M West; Berber Rouwé; Peter T Northcote; Michael V Berridge; St John Wakefield; John H Miller
Journal:  Cancer Res       Date:  2002-06-15       Impact factor: 12.701
  10 in total
  2 in total

1.  Synthetic studies of microtubule stabilizing agent peloruside A: an asymmetric synthesis of C10-C24 segment.

Authors:  Arun K Ghosh; Jae-Hun Kim
Journal:  Tetrahedron Lett       Date:  2003-09-13       Impact factor: 2.415

2.  Synthesis of Bioactive Natural Products by Asymmetric syn- and anti-Aldol Reactions.

Authors:  Arun K Ghosh; Zachary L Dawson
Journal:  Synthesis (Stuttg)       Date:  2009-09       Impact factor: 3.157
  2 in total

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