Total Synthesis of (−)-Zampanolide and Questionable Existence of (−)-Dactylolide as the Elusive Biosynthetic Precursor of (−)-Zampanolide in an Okinawan Sponge

2009 ◽  
Vol 11 (15) ◽  
pp. 3262-3265 ◽  
Author(s):  
Jun’ichi Uenishi ◽  
Takuya Iwamoto ◽  
Junichi Tanaka
Keyword(s):  
Total Synthesis ◽  
Biosynthetic Precursor ◽  
Questionable Existence

scholarly journals Bioinspired Oxidative Cyclization of the Geissoschizine Skeleton for the Enantioselective Total Synthesis of Mavacuran Alkaloids

2019 ◽  
Author(s):  
Maxime Jarret ◽  
Victor Turpin ◽  
Aurélien Tap ◽  
Jean-Francois Gallard ◽  
Cyrille Kouklovsky ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Oxidative Coupling ◽  
Indole Alkaloids ◽  
Oxidative Cyclization ◽  
Total Syntheses ◽  
Enantioselective Total Synthesis ◽  
Biosynthetic Precursor ◽  
Monoterpene Indole Alkaloids ◽  
Coupling Approach

We report the enantioselective total syntheses of mavacurans alkaloids, (+)-taberdivarine H, (+)-16-hydoxymethyl-pleiocarpamine, (+)-16-epi-pleiocarpamine, and their postulated biosynthetic precursor 16-formyl-pleiocarpamine. This family of monoterpene indole alkaloids is a target of choice since some of its members are subunits of intricate bisindole alkaloids such as bipleiophylline. Inspired by the biosynthetic hypothesis, we explored an oxidative coupling approach from the geissoschizine framework to form the N1-C16 bond. Quaternization of the aliphatic nitrogen was key to achieve the oxidative coupling induced by KHMDS/I<sub>2 </sub>since<sub> </sub>it hides the nucleophilicity of the aliphatic nitrogen and locks the required cis conformation.

Sceptrin as a Potential Biosynthetic Precursor to Complex Pyrrole—Imidazole Alkaloids: The Total Synthesis of Ageliferin.

ChemInform ◽  
2004 ◽  
Vol 35 (36) ◽  
Author(s):  
Phil S. Baran ◽  
Daniel P. O'Malley ◽  
Alexandros L. Zografos
Keyword(s):  
Total Synthesis ◽  
Biosynthetic Precursor

Biomimetic total synthesis of (±)-yezo'otogirin A

2014 ◽  
Vol 12 (16) ◽  
pp. 2519-2522 ◽  
Author(s):  
Hiu C. Lam ◽  
Kevin K. W. Kuan ◽  
Jonathan H. George
Keyword(s):  
Total Synthesis ◽  
Late Stage ◽  
Radical Cyclization ◽  
Biosynthetic Precursor ◽  
Oxidative Radical Cyclization

A concise total synthesis of (±)-yezo'otogirin A has been achieved via its presumed biosynthetic precursor using a late-stage biomimetic oxidative radical cyclization.

Enantioselective Total Synthesis of (+)-Iso-A82775C, a Proposed Biosynthetic Precursor of Chloropupukeananin

2017 ◽  
Vol 19 (4) ◽  
pp. 922-925 ◽  
Author(s):  
Takahiro Suzuki ◽  
Soichiro Watanabe ◽  
Susumu Kobayashi ◽  
Keiji Tanino
Keyword(s):  
Total Synthesis ◽  
Enantioselective Total Synthesis ◽  
Biosynthetic Precursor

Total synthesis of δ-(L-α-aminoadipyl)-L-cysteinyl-D-valine (ACV), a biosynthetic precursor of penicillins and cephalosporins

1979 ◽  
Vol 57 (11) ◽  
pp. 1388-1396 ◽  
Author(s):  
Saul Wolfe ◽  
Mark Gordon Jokinen
Keyword(s):  
Total Synthesis ◽  
Trifluoroacetic Acid ◽  
Title Compound ◽  
Biosynthetic Precursor ◽  
Oxidative Removal

The title compound has been synthesized as its disulfide by a classical route from the fully protected precursor N-BOC-S-trityl-δ-(L-α-aminoadipyl)-L-cysteinyl-D-valine bisbenzhydryl ester. Deprotection has been achieved by oxidative removal of the trityl group with iodine, followed by removal of BOC and benzhydryl using trifluoroacetic acid. The final product is obtained in 23% overall yield from D-valine.

Sign in / Sign up

Export Citation Format

Share Document