Literature DB >> 27701860

Total Synthesis of Aquatolide: Wolff Ring Contraction and Late-Stage Nozaki-Hiyama-Kishi Medium-Ring Formation.

Bin Wang1, Yuanzhen Xie1, Qin Yang2, Guozhu Zhang2, Zhenhua Gu1.   

Abstract

A total synthesis of the highly strained natural product aquatolide has been achieved. The synthesis featured a photoinduced Wolff ring contraction reaction for the construction of bicyclo[2.1.1]hexane from diazo compound with a bicyclo[2.2.1]heptane skeleton. The eight-membered enone was built by a late-stage intramolecular Nozaki-Hiyama-Kishi vinylation reaction of steric bulky vinyl iodide and aldehyde.

Entities:  

Year:  2016        PMID： 27701860     DOI： 10.1021/acs.orglett.6b02767

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


  3 in total

1.  Enantioselective Nozaki-Hiyama-Kishi allylation-lactonization for the syntheses of 3-substituted phthalides.

Authors:  Sharad V Kumbhar; Chinpiao Chen
Journal:  RSC Adv       Date:  2018-12-12       Impact factor: 4.036

Review 2.  The value of universally available raw NMR data for transparency, reproducibility, and integrity in natural product research.

Authors:  James B McAlpine; Shao-Nong Chen; Andrei Kutateladze; John B MacMillan; Giovanni Appendino; Andersson Barison; Mehdi A Beniddir; Maique W Biavatti; Stefan Bluml; Asmaa Boufridi; Mark S Butler; Robert J Capon; Young H Choi; David Coppage; Phillip Crews; Michael T Crimmins; Marie Csete; Pradeep Dewapriya; Joseph M Egan; Mary J Garson; Grégory Genta-Jouve; William H Gerwick; Harald Gross; Mary Kay Harper; Precilia Hermanto; James M Hook; Luke Hunter; Damien Jeannerat; Nai-Yun Ji; Tyler A Johnson; David G I Kingston; Hiroyuki Koshino; Hsiau-Wei Lee; Guy Lewin; Jie Li; Roger G Linington; Miaomiao Liu; Kerry L McPhail; Tadeusz F Molinski; Bradley S Moore; Joo-Won Nam; Ram P Neupane; Matthias Niemitz; Jean-Marc Nuzillard; Nicholas H Oberlies; Fernanda M M Ocampos; Guohui Pan; Ronald J Quinn; D Sai Reddy; Jean-Hugues Renault; José Rivera-Chávez; Wolfgang Robien; Carla M Saunders; Thomas J Schmidt; Christoph Seger; Ben Shen; Christoph Steinbeck; Hermann Stuppner; Sonja Sturm; Orazio Taglialatela-Scafati; Dean J Tantillo; Robert Verpoorte; Bin-Gui Wang; Craig M Williams; Philip G Williams; Julien Wist; Jian-Min Yue; Chen Zhang; Zhengren Xu; Charlotte Simmler; David C Lankin; Jonathan Bisson; Guido F Pauli
Journal:  Nat Prod Rep       Date:  2018-07-13       Impact factor: 13.423

Review 3.  Preparation and Synthetic Applications of Five-to-Seven-Membered Cyclic α-Diazo Monocarbonyl Compounds.

Authors:  Daniil Zhukovsky; Dmitry Dar'in; Olga Bakulina; Mikhail Krasavin
Journal:  Molecules       Date:  2022-03-21       Impact factor: 4.411
  3 in total

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