Literature DB >> 20694174

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

Amos B Smith1, Helmars Smits, Dae-Shik Kim.   

Abstract

Construction of the C(1)-C(25) southern fragments of both spirastrellolide A and B are described. Highlights of the syntheses include effective use of the three component anion relay chemistry (ARC) tactic recently introduced by our laboratory, a stereoselective spirocyclization via concomitant Ferrier reaction to elaborate the BC spiroketal and use of two dithiane unions to install the A ring as well as C(22)-C(25) fragment. The synthesis proceeded with longest linear sequences of 33 and 32 steps respectively for spirastrellolide A and spirastrellolide B.

Entities:  

Year:  2010        PMID： 20694174      PMCID： PMC2915457          DOI： 10.1016/j.tet.2010.01.082

Source DB:  PubMed          Journal:  Tetrahedron        ISSN： 0040-4020            Impact factor:   2.457


  23 in total

1.  Anion relay chemistry: an effective tactic for diversity oriented synthesis.

Authors:  Amos B Smith; Ming Xian
Journal:  J Am Chem Soc       Date:  2006-01-11       Impact factor: 15.419

2.  Synthesis of the C11-C23 fragment of spirastrellolide A. A ketal-tethered RCM approach to the construction of spiroketals.

Authors:  Jia Liu; Richard P Hsung
Journal:  Org Lett       Date:  2005-05-26       Impact factor: 6.005

3.  Toward the total synthesis of spirastrellolide A. Part 1: Strategic considerations and preparation of the southern domain.

Authors:  Alois Fürstner; Michaël D B Fenster; Bernhard Fasching; Cédrickx Godbout; Karin Radkowski
Journal:  Angew Chem Int Ed Engl       Date:  2006-08-18       Impact factor: 15.336

4.  Spirastrellolide B reveals the absolute configuration of the spirastrellolide macrolide core.

Authors:  Kaoru Warabi; David E Williams; Brian O Patrick; Michel Roberge; Raymond J Andersen
Journal:  J Am Chem Soc       Date:  2007-01-24       Impact factor: 15.419

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

Authors:  Ian Paterson; Edward A Anderson; Stephen M Dalby; Jong Ho Lim; Philip Maltas; Christian Moessner
Journal:  Chem Commun (Camb)       Date:  2006-09-20       Impact factor: 6.222

6.  Toward the total synthesis of spirastrellolide A. Part 3: intelligence gathering and preparation of a ring-expanded analogue.

Authors:  Alois Fürstner; Bernhard Fasching; Gregory W O'Neil; Michaël D B Fenster; Cédrickx Godbout; Julien Ceccon
Journal:  Chem Commun (Camb)       Date:  2007-06-26       Impact factor: 6.222

7.  Toward the synthesis of spirastrellolide A: construction of two C1-C25 diastereomers containing the BC-spiroacetal.

Authors:  Ian Paterson; Edward A Anderson; Stephen M Dalby; Olivier Loiseleur
Journal:  Org Lett       Date:  2005-09-15       Impact factor: 6.005

8.  Spirastrellolide A, an antimitotic macrolide isolated from the Caribbean marine sponge Spirastrella coccinea.

Authors:  David E Williams; Michel Roberge; Rob Van Soest; Raymond J Andersen
Journal:  J Am Chem Soc       Date:  2003-05-07       Impact factor: 15.419

9.  Synthesis of the C1-C23 fragment of Spirastrellolide A.

Authors:  Jin-Haek Yang; Jia Liu; Richard P Hsung
Journal:  Org Lett       Date:  2008-05-17       Impact factor: 6.005

10.  Gram-scale synthesis of (+)-spongistatin 1: development of an improved, scalable synthesis of the F-ring subunit, fragment union, and final elaboration.

Authors:  Amos B Smith; Takashi Tomioka; Christina A Risatti; Jeffrey B Sperry; Chris Sfouggatakis
Journal:  Org Lett       Date:  2008-08-28       Impact factor: 6.005
View more
  11 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.  Evolution of Anion Relay Chemistry: Construction of Architecturally Complex Natural Products.

Authors:  Yifan Deng; Amos B Smith
Journal:  Acc Chem Res       Date:  2020-04-09       Impact factor: 22.384

3.  Design, synthesis, and biological evaluation of diminutive forms of (+)-spongistatin 1: lessons learned.

Authors:  Amos B Smith; Christina A Risatti; Onur Atasoylu; Clay S Bennett; Junke Liu; Hongsheng Cheng; Karen TenDyke; Qunli Xu
Journal:  J Am Chem Soc       Date:  2011-08-12       Impact factor: 15.419

4.  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

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.  Through-bond/through-space anion relay chemistry exploiting vinylepoxides as bifunctional linchpins.

Authors:  Ming Z Chen; Osvaldo Gutierrez; Amos B Smith
Journal:  Angew Chem Int Ed Engl       Date:  2013-12-16       Impact factor: 15.336

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

8.  Synthesis of the C9-C25 Subunit of Spirastrellolide B.

Authors:  Soma Maitra; Mahipal Bodugam; Salim Javed; Paul R Hanson
Journal:  Org Lett       Date:  2016-06-14       Impact factor: 6.005

9.  Total Synthesis of (-)-Mandelalide A Exploiting Anion Relay Chemistry (ARC): Identification of a Type II ARC/CuCN Cross-Coupling Protocol.

Authors:  Minh H Nguyen; Masashi Imanishi; Taichi Kurogi; Amos B Smith
Journal:  J Am Chem Soc       Date:  2016-03-08       Impact factor: 15.419

10.  An Effective Bifunctional Aldehyde Linchpin for Type II Anion Relay Chemistry: Development and Application to the Synthesis of a C16-C29 Fragment of Rhizopodin.

Authors:  Bruno Melillo; Ming Z Chen; Roberto Forestieri; Amos B Smith
Journal:  Org Lett       Date:  2015-12-07       Impact factor: 6.005
View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.