Literature DB >> 29375135

Total synthesis of (+)-lysergic acid.

Rentaro Kanno1, Satoshi Yokoshima2, Motomu Kanai1, Tohru Fukuyama2.   

Abstract

A total synthesis of (+)-lysergic acid, which features the C-C bond formation between C10 and C11 via cleavage of an aziridine ring, was accomplished.

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Year:  2017        PMID： 29375135     DOI： 10.1038/ja.2017.80

Source DB:  PubMed          Journal:  J Antibiot (Tokyo)        ISSN： 0021-8820            Impact factor:   2.649


  18 in total

1.  Total synthesis of dihydrolysergic acid and dihydrolysergol: development of a divergent synthetic strategy applicable to rapid assembly of D-ring analogs.

Authors:  Kiyoun Lee; Yam B Poudel; Christopher M Glinkerman; Dale L Boger
Journal:  Tetrahedron       Date:  2015-09-02       Impact factor: 2.457

2.  Asymmetric aldol additions: use of titanium tetrachloride and (-)-sparteine for the soft enolization of N-acyl oxazolidinones, oxazolidinethiones, and thiazolidinethiones.

Authors:  M T Crimmins; B W King; E A Tabet; K Chaudhary
Journal:  J Org Chem       Date:  2001-02-09       Impact factor: 4.354

3.  Enantioselective Total Synthesis of (+)-Lysergol: A Formal anti-Carbopalladation/Heck Cascade as the Key Step.

Authors:  Bastian Milde; Martin Pawliczek; Peter G Jones; Daniel B Werz
Journal:  Org Lett       Date:  2017-03-30       Impact factor: 6.005

4.  Stereocontrolled syntheses of epimeric 3-aryl-6-phenyl-1-oxa-7-azaspiro(4.5)decane NK-1 receptor antagonist precursors.

Authors:  J J Kulagowski; N R Curtis; C J Swain; B J Williams
Journal:  Org Lett       Date:  2001-03-08       Impact factor: 6.005

5.  Total Syntheses of (-)-Hibiscone C and Lysergine: A Cyclization/Fragmentation Strategy.

Authors:  Yandong Lu; Haosen Yuan; Shijie Zhou; Tuoping Luo
Journal:  Org Lett       Date:  2017-01-20       Impact factor: 6.005

6.  Regiocontrol of the palladium-catalyzed tin hydride addition to Z-enynols: remarkable Z-directing effects.

Authors:  Abdallah Hamze; Olivier Provot; Jean-Daniel Brion; Mouâd Alami
Journal:  J Org Chem       Date:  2007-04-14       Impact factor: 4.354

7.  Formal total synthesis of (+)-lysergic acid via zinc(II)-mediated regioselective ring-opening reduction of 2-alkynyl-3-indolyloxirane.

Authors:  Akira Iwata; Shinsuke Inuki; Shinya Oishi; Nobutaka Fujii; Hiroaki Ohno
Journal:  J Org Chem       Date:  2011-06-08       Impact factor: 4.354

Review 8.  Ergot alkaloids: synthetic approaches to lysergic acid and clavine alkaloids.

Authors:  Haichao Liu; Yanxing Jia
Journal:  Nat Prod Rep       Date:  2017-04-05       Impact factor: 13.423

9.  Total synthesis of (+/-)-lysergic acid, lysergol, and isolysergol by palladium-catalyzed domino cyclization of amino allenes bearing a bromoindolyl group.

Authors:  Shinsuke Inuki; Shinya Oishi; Nobutaka Fujii; Hiroaki Ohno
Journal:  Org Lett       Date:  2008-10-29       Impact factor: 6.005

10.  A new synthesis of lysergic acid.

Authors:  James B Hendrickson; Jian Wang
Journal:  Org Lett       Date:  2004-01-08       Impact factor: 6.005
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