Literature DB >> 14871089

Toward a general route to the eunicellin diterpenes: the asymmetric total synthesis of deacetoxyalcyonin acetate.

Gary A Molander1, David J St Jean, Julia Haas.   

Abstract

A novel approach to the hydroisobenzofuran core utilizing a TiCl4-mediated [4+3] annulation is reported. This [4+3] annulation protocol provides a short, general route to the hydroisobenzofuran core present in the eunicellin diterpenes. Using this annulation, a short synthesis (17 steps) of deacetoxyalcyonin acetate, a member of the eunicellin family, has been achieved.

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Year:  2004        PMID: 14871089     DOI: 10.1021/ja0398464

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  9 in total

1.  A general route toward the synthesis of the cladiellin skeleton utilizing a SmI2-mediated cyclization.

Authors:  Gary A Molander; Barbara Czakó; David J St Jean
Journal:  J Org Chem       Date:  2006-02-03       Impact factor: 4.354

Review 2.  Navigating the Chiral Pool in the Total Synthesis of Complex Terpene Natural Products.

Authors:  Zachary G Brill; Matthew L Condakes; Chi P Ting; Thomas J Maimone
Journal:  Chem Rev       Date:  2017-03-15       Impact factor: 60.622

3.  Establishing the absolute configuration of the asbestinins: enantioselective total synthesis of 11-acetoxy-4-deoxyasbestinin D.

Authors:  Michael T Crimmins; J Michael Ellis
Journal:  J Am Chem Soc       Date:  2005-12-14       Impact factor: 15.419

Review 4.  Applications of Norrish type I and II reactions in the total synthesis of natural products: a review.

Authors:  Sasadhar Majhi
Journal:  Photochem Photobiol Sci       Date:  2021-09-18       Impact factor: 3.982

5.  A unified strategy for enantioselective total synthesis of cladiellin and briarellin diterpenes: total synthesis of briarellins E and F and the putative structure of alcyonin and revision of its structure assignment.

Authors:  Olivier Corminboeuf; Larry E Overman; Lewis D Pennington
Journal:  J Org Chem       Date:  2009-08-07       Impact factor: 4.354

6.  Synthesis and Evaluation of a 2,11-Cembranoid-Inspired Library.

Authors:  Amanda J Welford; John J Caldwell; Manjuan Liu; Meirion Richards; Nathan Brown; Cara Lomas; Graham J Tizzard; Mateusz B Pitak; Simon J Coles; Suzanne A Eccles; Florence I Raynaud; Ian Collins
Journal:  Chemistry       Date:  2016-03-01       Impact factor: 5.236

Review 7.  Photochemical Approaches to Complex Chemotypes: Applications in Natural Product Synthesis.

Authors:  Markus D Kärkäs; John A Porco; Corey R J Stephenson
Journal:  Chem Rev       Date:  2016-04-27       Impact factor: 60.622

Review 8.  A review on various aspects of organic synthesis using Comins' reagent.

Authors:  Duraipandi Devi Priya; Chetan Lakshman; Selvaraj Mohana Roopan
Journal:  Mol Divers       Date:  2021-01-03       Impact factor: 2.943

9.  Towards a general diastereoselective route to oxabicyclo[3.2.1]octanes via a gold-catalysed cascade reaction.

Authors:  Junkai Fu; Yueqing Gu; Hao Yuan; Tuoping Luo; Song Liu; Yu Lan; Jianxian Gong; Zhen Yang
Journal:  Nat Commun       Date:  2015-10-16       Impact factor: 14.919

  9 in total

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