Literature DB >> 18568055

A Short Synthesis of (S)-(+)-Siphonodiol.

Benjamin W Gung1, Derek T Craft, Jessica Truelove.   

Abstract

A short synthesis of the enantiomer of the polyacetylenic natural product siphonodiol is described. The synthesis is based on the strategy of taking advantage of the hidden symmetry of the target molecule and minimizing the use of protecting groups, thereby reducing the total number of steps and increasing the overall efficiency.

Entities:  

Year:  2007        PMID： 18568055      PMCID： PMC2031836          DOI： 10.1016/j.tetasy.2007.05.034

Source DB:  PubMed          Journal:  Tetrahedron Asymmetry        ISSN： 0957-4166


  6 in total

1.  Synthesis of marine polyacetylenes callyberynes A-C by transition-metal-catalyzed cross-coupling reactions to sp centers.

Authors:  Susana López; Francisco Fernandez-Trillo; Pilar Midón; Luis Castedo; Carlos Saa
Journal:  J Org Chem       Date:  2006-03-31       Impact factor: 4.354

2.  Synthesis of diynes and tetraynes from in situ desilylation/dimerization of acetylenes.

Authors:  M A Heuft; S K Collins; G P Yap; A G Fallis
Journal:  Org Lett       Date:  2001-09-06       Impact factor: 6.005

3.  First stereoselective syntheses of (-)-siphonodiol and (-)-tetrahydrosiphonodiol, bioactive polyacetylenes from marine sponges.

Authors:  Susana López; Francisco Fernández-Trillo; Pilar Midón; Luis Castedo; Carlos Saá
Journal:  J Org Chem       Date:  2005-08-05       Impact factor: 4.354

4.  Total synthesis of (-)-minquartynoic acid: an anti-cancer, anti-HIV natural product.

Authors:  Benjamin W Gung; Hamilton Dickson
Journal:  Org Lett       Date:  2002-07-25       Impact factor: 6.005

5.  Remarkable reactivity difference in oxygen-substituted versus non-oxygen-substituted bromoalkynes in Cu(I)-catalyzed cross-coupling reactions: total synthesis of (-)-S-18-hydroxyminquartynoic acid.

Authors:  Benjamin W Gung; Godwin Kumi
Journal:  J Org Chem       Date:  2003-07-25       Impact factor: 4.354

6.  Total synthesis of (S)-(-)-(E)-15,16-dihydrominquartynoic acid: a highly potent anticancer agent.

Authors:  Benjamin W Gung; Godwin Kumi
Journal:  J Org Chem       Date:  2004-05-14       Impact factor: 4.354
  6 in total
  2 in total

1.  Polyacetylene diols with antiproliferative and driving Th1 polarization effects from the marine sponge Callyspongia sp.

Authors:  Akemi Umeyama; Nanae Matsuoka; Rieko Mine; Akemi Nakata; Eri Arimoto; Miwa Matsui; Noboru Shoji; Shigenobu Arihara; Masao Takei; Toshihiro Hashimoto
Journal:  J Nat Med       Date:  2009-10-03       Impact factor: 2.343

Review 2.  Cytotoxic Compounds Derived from Marine Sponges. A Review (2010-2012).

Authors:  Roberto Mioso; Francisco J Toledo Marante; Ranilson de Souza Bezerra; Flávio Valadares Pereira Borges; Bárbara V de Oliveira Santos; Irma Herrera Bravo de Laguna
Journal:  Molecules       Date:  2017-01-28       Impact factor: 4.411
  2 in total

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