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Literature DB >> 24962149

Bioinspired total synthesis of sespenine.

Yu Sun¹, Pengxi Chen, Deliang Zhang, Martin Baunach, Christian Hertweck, Ang Li.

Abstract

The first total synthesis of sespenine, a rare indole sesquiterpenoid from a mangrove endophyte, has been accomplished. A bioinspired aza-Prins/Friedel-Crafts/retro Friedel-Crafts cascade reaction assembles the bridged tetrahydroquinoline core. Further investigations on the aza-Prins cyclization imply that the C3 configuration of the hydroxyindolenine intermediate is crucial to the biosynthesis of sespenine and its congener xiamycin A.

Entities: Chemical

Keywords: biomimetic synthesis; cyclization; heterocycles; natural products; total synthesis

Mesh：

Substances：
Sesquiterpenes

Year: 2014 PMID： 24962149 DOI： 10.1002/anie.201404191

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

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Cited

9 in total

1. Total Synthesis of Oridamycins A and B.

Authors: Adam H Trotta
Journal: Org Lett Date: 2015-06-12 Impact factor: 6.005

2. A 5 + 1 Protic Acid Assisted Aza-Pummerer Approach for Synthesis of 4-Chloropiperidines from Homoallylic Amines.

Authors: Rene Ebule; Sagar Mudshinge; Michael H Nantz; Mark S Mashuta; Gerald B Hammond; Bo Xu
Journal: J Org Chem Date: 2019-02-27 Impact factor: 4.354

3. Synthesis of Enantioenriched Indolines by a Conjugate Addition/Asymmetric Protonation/Aza-Prins Cascade Reaction.

Authors: Blake E Daniels; Jane Ni; Sarah E Reisman
Journal: Angew Chem Int Ed Engl Date: 2016-02-04 Impact factor: 15.336

4. Selective syntheses of leuconolam, leuconoxine, and mersicarpine alkaloids from a common intermediate through regiocontrolled cyclizations by Staudinger reactions†Electronic supplementary information (ESI) available: Experimental details and procedures, compound characterization data, copies of ¹H and ¹³C NMR spectra for new compounds. See DOI: 10.1039/c4qo00312hClick here for additional data file.

Authors: Zining Li; Qian Geng; Zhe Lv; Beau P Pritchett; Katsuaki Baba; Yoshitaka Numajiri; Brian M Stoltz; Guangxin Liang
Journal: Org Chem Front Date: 2015-01-27 Impact factor: 5.281

Bioinspired total synthesis of sespenine.

1. Total Synthesis of Oridamycins A and B.

2. A 5 + 1 Protic Acid Assisted Aza-Pummerer Approach for Synthesis of 4-Chloropiperidines from Homoallylic Amines.

3. Synthesis of Enantioenriched Indolines by a Conjugate Addition/Asymmetric Protonation/Aza-Prins Cascade Reaction.

5. Total synthesis and antiviral activity of indolosesquiterpenoids from the xiamycin and oridamycin families.

6. Cryptic indole hydroxylation by a non-canonical terpenoid cyclase parallels bacterial xenobiotic detoxification.

7. Frogolide - An Unprecedented Sesquiterpene Macrolactone from Scent Glands of African Frogs.

8. Characterization of the flavoenzyme XiaK as an N-hydroxylase and implications in indolosesquiterpene diversification.

Review 9. Recent Achievements in Total Synthesis for Integral Structural Revisions of Marine Natural Products.