Literature DB >> 23161829

Total synthesis of (-)-acetylaranotin.

Hideto Fujiwara1, Taichi Kurogi, Shun Okaya, Kentaro Okano, Hidetoshi Tokuyama.   

Abstract

The key step in this total synthesis of (-)-acetylaranotin is the efficient formation of the characteristic dihydrooxepine ring from cyclohexenone through an unusual vinylogous Rubottom oxidation and a regioselective Baeyer-Villiger oxidation. (-)-Acetylaranotin is obtained in 22 steps from commercially available L-Cbz-tyrosine (Cbz=benzyloxycarbonyl).
Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

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Year:  2012        PMID： 23161829     DOI： 10.1002/anie.201207307

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  8 in total

1.  Total Synthesis of Oxepin and Dihydrooxepin Containing Natural Products.

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2.  A Racemic Naphthyl-Coumarin-Based Probe for Quantitative Enantiomeric Excess Analysis of Amino Acids and Enantioselective Sensing of Amines and Amino Alcohols.

Authors:  Jia-Yi Li; Li Wang; Li-Ping Yin; Xin-Meng Jiang; Kai Guo; Chun Zhang; Shan-Shan Yu; Xiao-Qi Yu; Qin Wang
Journal:  ChemistryOpen       Date:  2022-06       Impact factor: 2.630

Review 3.  Epidithiodioxopiperazines. occurrence, synthesis and biogenesis.

Authors:  Timothy R Welch; Robert M Williams
Journal:  Nat Prod Rep       Date:  2014-10       Impact factor: 13.423

4.  Biosynthetic pathway for the epipolythiodioxopiperazine acetylaranotin in Aspergillus terreus revealed by genome-based deletion analysis.

Authors:  Chun-Jun Guo; Hsu-Hua Yeh; Yi-Ming Chiang; James F Sanchez; Shu-Ling Chang; Kenneth S Bruno; Clay C C Wang
Journal:  J Am Chem Soc       Date:  2013-05-01       Impact factor: 15.419

5.  General approach for preparing epidithiodioxopiperazines from trioxopiperazine precursors: enantioselective total syntheses of (+)- and (-)-gliocladine C, (+)-leptosin D, (+)-T988C, (+)-bionectin A, and (+)-gliocladin A.

Authors:  John E DeLorbe; David Horne; Richard Jove; Steven M Mennen; Sangkil Nam; Fang-Li Zhang; Larry E Overman
Journal:  J Am Chem Soc       Date:  2013-03-01       Impact factor: 15.419

6.  General synthetic approach to functionalized dihydrooxepines.

Authors:  K C Nicolaou; Ruocheng Yu; Lei Shi; Quan Cai; Min Lu; Philipp Heretsch
Journal:  Org Lett       Date:  2013-04-04       Impact factor: 6.005

7.  Enantioselective Synthesis of (-)-Acetylapoaranotin.

Authors:  Haoxuan Wang; Clinton J Regan; Julian A Codelli; Paola Romanato; Angela L A Puchlopek-Dermenci; Sarah E Reisman
Journal:  Org Lett       Date:  2017-03-28       Impact factor: 6.005

Review 8.  Recent Advances in Substrate-Controlled Asymmetric Induction Derived from Chiral Pool α-Amino Acids for Natural Product Synthesis.

Authors:  Seung-Mann Paek; Myeonggyo Jeong; Jeyun Jo; Yu Mi Heo; Young Taek Han; Hwayoung Yun
Journal:  Molecules       Date:  2016-07-21       Impact factor: 4.411
  8 in total

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