Literature DB >> 11554814

Formal total synthesis of (+/-)-alpha- and beta-cedrene by preparation of cedrone. Construction of the tricyclic carbon skeleton by the use of a highly efficient intramolecular Khand annulation.

W J Kerr1, M McLaughlin, A J Morrison, P L Pauson.   

Abstract

The cedrene carbon skeleton was rapidly assembled from a simple monocyclic precursor by the strategic use of a high yielding intramolecular Khand cyclization reaction. Further synthetic manipulations provided a concise formal total synthesis of alpha- and beta-cedrene. Reaction: see text.

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Year:  2001        PMID: 11554814     DOI: 10.1021/ol016054a

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  5 in total

1.  Concise, enantioselective total synthesis of (-)-alstonerine.

Authors:  Kenneth A Miller; Stephen F Martin
Journal:  Org Lett       Date:  2007-02-14       Impact factor: 6.005

2.  A Complementary Process to Pauson-Khand-Type Annulation Reactions for the Construction of Fully Substituted Cyclopentenones.

Authors:  Adam B Millham; Matthew J Kier; Robert M Leon; Rajdip Karmakar; Zachary D Stempel; Glenn C Micalizio
Journal:  Org Lett       Date:  2019-01-07       Impact factor: 6.005

3.  Spirodiepoxide strategy to the C ring of pectenotoxin 4: synthesis of the C1-C19 sector.

Authors:  Sipak Joyasawal; Stephen D Lotesta; N G Akhmedov; Lawrence J Williams
Journal:  Org Lett       Date:  2010-03-05       Impact factor: 6.005

Review 4.  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 5.  Application of Pauson-Khand reaction in the total synthesis of terpenes.

Authors:  Majid M Heravi; Leila Mohammadi
Journal:  RSC Adv       Date:  2021-11-29       Impact factor: 4.036

  5 in total

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