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Literature DB >> 22273402

A concise total synthesis of (±)- and (-)-okilactomycin D.

Abstract

The spirotetronate okilactomycin D (7) has been efficiently synthesized by a route featuring a substrate-controlled, diastereoselective (8:1) intramolecular Diels-Alder (IMDA) reaction of 11. The assigned absolute configuration of (-)-7 was confirmed.

Entities: Chemical Disease Species

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Year: 2012 PMID： 22273402 PMCID： PMC3272355 DOI： 10.1021/ol203355g

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

14 in total

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Authors: R Nakai; S Kakita; A Asai; S Chiba; S Akinaga; T Mizukami; Y Yamashita
Journal: J Antibiot (Tokyo) Date: 2001-10 Impact factor: 2.649

2. A Diels-Alder macrocyclization enables an efficient asymmetric synthesis of the antibacterial natural product abyssomicin C.

Authors: Christoph W Zapf; Bryce A Harrison; Carmen Drahl; Erik J Sorensen
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3. Genetic characterization of the chlorothricin gene cluster as a model for spirotetronate antibiotic biosynthesis.

Authors: Xin-Ying Jia; Zhen-Hua Tian; Lei Shao; Xu-Dong Qu; Qun-Fei Zhao; Jian Tang; Gong-Li Tang; Wen Liu
Journal: Chem Biol Date: 2006-06

4. Selective synthesis of epolactaene featuring efficient construction of methyl (Z)-2-iodo-2-butenoate and (2R,3S,4S)-2-trimethylsilyl-2,3-epoxy-4-methyl- gamma-butyrolactone.

Authors: Ze Tan; Ei-Ichi Negishi
Journal: Org Lett Date: 2006-06-22 Impact factor: 6.005

5. New cholesterol biosynthesis inhibitors MC-031 (O-demethylchlorothricin), -032 (O-demethylhydroxychlorothricin), -033 and -034.

Authors: A Kawashima; Y Nakamura; Y Ohta; T Akama; M Yamagishi; K Hanada
Journal: J Antibiot (Tokyo) Date: 1992-02 Impact factor: 2.649

6. Maklamicin, an antibacterial polyketide from an endophytic Micromonospora sp.

Authors: Yasuhiro Igarashi; Hiromu Ogura; Kazuo Furihata; Naoya Oku; Chantra Indananda; Arinthip Thamchaipenet
Journal: J Nat Prod Date: 2011-03-09 Impact factor: 4.050

7. Isolation, structure elucidation, and antitumor activity of spirohexenolides A and B.

Authors: MinJin Kang; Brian D Jones; Alexander L Mandel; Justin C Hammons; Antonio G DiPasquale; Arnold L Rheingold; James J La Clair; Michael D Burkart
Journal: J Org Chem Date: 2009-12-04 Impact factor: 4.354

8. Discovery of okilactomycin and congeners from Streptomyces scabrisporus by antisense differential sensitivity assay targeting ribosomal protein S4.

Authors: Chaowei Zhang; John G Ondeyka; Deborah L Zink; Angela Basilio; Francisca Vicente; Oscar Salazar; Olga Genilloud; Karen Dorso; Mary Motyl; Kevin Byrne; Sheo B Singh
Journal: J Antibiot (Tokyo) Date: 2009-01-09 Impact factor: 2.649

9. Chemoenzymatic synthesis of the C10-C23 segment of dictyostatin.

Authors: Evgeny Prusov; Hartmut Röhm; Martin E Maier
Journal: Org Lett Date: 2006-03-16 Impact factor: 6.005

10. Okilactomycin, a novel antibiotic produced by a Streptomyces species. I. Taxonomy, fermentation, isolation and characterization.

Authors: H Imai; K Suzuki; M Morioka; Y Numasaki; S Kadota; K Nagai; T Sato; M Iwanami; T Saito
Journal: J Antibiot (Tokyo) Date: 1987-11 Impact factor: 2.649

1 in total

Review 1. Spirotetronate polyketides as leads in drug discovery.

Authors: Michelle H Lacoske; Emmanuel A Theodorakis
Journal: J Nat Prod Date: 2014-12-01 Impact factor: 4.050

1 in total