Literature DB >> 25083002

Synthetic studies on lemonomycin: construction of the tetracyclic core.

Alberto Jiménez-Somarribas1, Robert M Williams2.   

Abstract

A substrate-induced stereocontrol strategy was used to gain access to the tetracyclic core of (-)-lemonomycin. An advanced intermediate was prepared from a known substituted tyrosinol through a 16-step sequence, which involved a Pictet-Spengler reaction, a [3+2] dipolar cycloaddition and an enamide hydrogenation.

Entities:  

Keywords:  (-)-Lemonomycin; Pictet-Spengler reaction; Tetrahydroisoquinoline antitumor antibiotics; [3+2] dipolar cycloaddition

Year:  2013        PMID： 25083002      PMCID： PMC4114395          DOI： 10.1016/j.tet.2013.05.009

Source DB:  PubMed          Journal:  Tetrahedron        ISSN： 0040-4020            Impact factor:   2.457


  18 in total

Review 1.  Chemistry and biology of the tetrahydroisoquinoline antitumor antibiotics.

Authors:  Jack D Scott; Robert M Williams
Journal:  Chem Rev       Date:  2002-05       Impact factor: 60.622

2.  ISOLATION AND CHARACTERIZATION OF LEMONOMYCIN, A NEW ANTIBIOTIC.

Authors:  H A WHALEY; E L PATTERSON; M DANN; A J SHAY; J N PORTER
Journal:  Antimicrob Agents Chemother (Bethesda)       Date:  1964

3.  Total synthesis of ecteinascidin 743.

Authors:  Jinchun Chen; Xiaochuan Chen; Michèle Bois-Choussy; Jieping Zhu
Journal:  J Am Chem Soc       Date:  2006-01-11       Impact factor: 15.419

4.  Total synthesis of (-)-lemonomycin.

Authors:  Atsushi Yoshida; Michinori Akaiwa; Tomohiro Asakawa; Yoshitaka Hamashima; Satoshi Yokoshima; Tohru Fukuyama; Toshiyuki Kan
Journal:  Chemistry       Date:  2012-07-30       Impact factor: 5.236

5.  Total Synthesis of (-)-Tetrazomine and Determination of Its Stereochemistry This work was supported by the National Institutes of Health (Grant CA85419). We are grateful to Yamanouchi Pharmaceutical Co. for providing a generous gift of natural tetrazomine.

Authors:  Jack D. Scott; Robert M. Williams
Journal:  Angew Chem Int Ed Engl       Date:  2001-04-17       Impact factor: 15.336

6.  The total synthesis of (--)-lemonomycin.

Authors:  Eric R Ashley; Ernest G Cruz; Brian M Stoltz
Journal:  J Am Chem Soc       Date:  2003-12-10       Impact factor: 15.419

7.  DC-52, a novel antitumor antibiotic. 2. Isolation, physico-chemical characteristics and structure determination.

Authors:  K Takahashi; F Tomita
Journal:  J Antibiot (Tokyo)       Date:  1983-05       Impact factor: 2.649

8.  Nocathiacins, new thiazolyl peptide antibiotics from Nocardia sp. I. Taxonomy, fermentation and biological activities.

Authors:  Wenying Li; John E Leet; Helen A Ax; Donald R Gustavson; Daniel M Brown; Laura Turner; Kimberly Brown; Junius Clark; Hyekyung Yang; Joan Fung-Tomc; Kin S Lam
Journal:  J Antibiot (Tokyo)       Date:  2003-03       Impact factor: 2.649

9.  MJ347-81F4 A & B, novel antibiotics from Amycolatopsis sp.: taxonomic characteristics, fermentation, and antimicrobial activity.

Authors:  T Sasaki; T Otani; H Matsumoto; N Unemi; M Hamada; T Takeuchi; M Hori
Journal:  J Antibiot (Tokyo)       Date:  1998-08       Impact factor: 2.649

10.  Thiazomycins, thiazolyl peptide antibiotics from Amycolatopsis fastidiosa.

Authors:  Chaowei Zhang; Kithsiri Herath; Hiranthi Jayasuriya; John G Ondeyka; Deborah L Zink; James Occi; Gwyneth Birdsall; Jayashree Venugopal; Misti Ushio; Bruce Burgess; Prakash Masurekar; John F Barrett; Sheo B Singh
Journal:  J Nat Prod       Date:  2009-05-22       Impact factor: 4.050
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  2 in total

Review 1.  Potent Antibiotic Lemonomycin: A Glimpse of Its Discovery, Origin, and Chemical Synthesis.

Authors:  Shunan Tao; Yang Wang; Ran Hong; Sha-Hua Huang
Journal:  Molecules       Date:  2022-07-05       Impact factor: 4.927

Review 2.  The Pictet-Spengler Reaction Updates Its Habits.

Authors:  Andrea Calcaterra; Laura Mangiardi; Giuliano Delle Monache; Deborah Quaglio; Silvia Balducci; Simone Berardozzi; Antonia Iazzetti; Roberta Franzini; Bruno Botta; Francesca Ghirga
Journal:  Molecules       Date:  2020-01-19       Impact factor: 4.411
  2 in total

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