Bioinspired Total Synthesis of the Dimeric Indole Alkaloid (+)-Haplophytine by Direct Coupling and Late-Stage Oxidative Rearrangement

2016 ◽  
Vol 55 (48) ◽  
pp. 15157-15161 ◽  
Author(s):  
Hitoshi Satoh ◽  
Ken-ichi Ojima ◽  
Hirofumi Ueda ◽  
Hidetoshi Tokuyama
Keyword(s):  
Total Synthesis ◽  
Late Stage ◽  
Indole Alkaloid ◽  
Direct Coupling ◽  
Oxidative Rearrangement

Bioinspired Total Synthesis of the Dimeric Indole Alkaloid (+)-Haplophytine by Direct Coupling and Late-Stage Oxidative Rearrangement

2016 ◽  
Vol 128 (48) ◽  
pp. 15381-15385
Author(s):  
Hitoshi Satoh ◽  
Ken-ichi Ojima ◽  
Hirofumi Ueda ◽  
Hidetoshi Tokuyama
Keyword(s):  
Total Synthesis ◽  
Late Stage ◽  
Indole Alkaloid ◽  
Direct Coupling ◽  
Oxidative Rearrangement

Convergent Total Synthesis of Principinol D, a Rearranged Kaurane Diterpenoid

2019 ◽  
Author(s):  
Timothy Newhouse ◽  
Aneta Turlik ◽  
Yifeng Chen ◽  
Anthony Scruse
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Late Stage ◽  
Membered Ring ◽  
Entry Point ◽  
Ketone Reduction ◽  
Coupling Approach

<div> <p>The total synthesis of principinol D, a rearranged kaurane diterpenoid, is reported. This grayanane natural product is constructed via a convergent fragment coupling approach, wherein the central 7-membered ring is synthesized at a late stage. The bicyclo[3.2.1]octane fragment is accessed by a Ni-catalyzed α-vinylation reaction. Strategic reductions include a diastereoselective SmI<sub>2</sub>-mediated ketone reduction with PhSH and a new protocol for selective ester reduction in the presence of ketones. The convergent strategy reported herein may be an entry point to the larger class of kaurane diterpenoids.</p> </div>

The Total Synthesis of Rhabdastrellic Acid A

2018 ◽  
Author(s):  
Yaroslav Boyko ◽  
Christopher Huck ◽  
David Sarlah
Keyword(s):  
Total Synthesis ◽  
Late Stage ◽  
Cross Coupling ◽  
Side Chains ◽  
General Strategy ◽  
Modular Approach ◽  
Linear Sequence ◽  
Generating Sequence ◽  
First Time

<div>The first total synthesis of rhabdastrellic acid A, a highly cytotoxic isomalabaricane triterpenoid, has been accomplished in a linear sequence of 14 steps from commercial geranylacetone. The prominently strained <i>trans-syn-trans</i>-perhydrobenz[<i>e</i>]indene core characteristic of the isomalabaricanes is efficiently accessed in a selective manner for the first time through a rapid, complexity-generating sequence incorporating a reductive radical polyene cyclization, an unprecedented oxidative Rautenstrauch cycloisomerization, and umpolung 𝛼-substitution of a <i>p</i>-toluenesulfonylhydrazone with in situ reductive transposition. A late-stage cross-coupling in concert with a modular approach to polyunsaturated side chains renders this a general strategy for the synthesis of numerous family members of these synthetically challenging and hitherto inaccessible marine triterpenoids.</div>

Total syntheses and antiproliferative activities of prenostodione and its analogues

2021 ◽  
Author(s):  
Aldahir Ramos Orea ◽  
María Teresa Ramírez-Apan ◽  
Rosa M. Chávez-Santos ◽  
Rodrigo Aguayo-Ortiz ◽  
Clara I Espitia ◽  
...  
Keyword(s):  
Carboxylic Acid ◽  
Total Synthesis ◽  
Indole Alkaloid ◽  
Total Syntheses ◽  
Antiproliferative Activities

A high-yielding total synthesis of the indole alkaloid prenostodione was completed in 4 steps and 44% overall yield from 1H-indole-3-carboxylic acid. The expedient syntheses of prenostodiones containing distinct substituents at...

ChemInform Abstract: The First Total Synthesis of (-)-Mitragynine, an Analgesic Indole Alkaloid in Mitragyna speciosa.

ChemInform ◽  
2010 ◽  
Vol 27 (15) ◽  
pp. no-no
Author(s):  
H. TAKAYAMA ◽  
M. MAEDA ◽  
S. OHBAYASHI ◽  
M. KITAJIMA ◽  
S. SAKAI ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Indole Alkaloid ◽  
Mitragyna Speciosa

Formal Total Synthesis of Diazonamide A by Indole Oxidative Rearrangement

2016 ◽  
Vol 22 (31) ◽  
pp. 10867-10876 ◽  
Author(s):  
Nadège David ◽  
Raffaele Pasceri ◽  
Russell R. A. Kitson ◽  
Alexandre Pradal ◽  
Christopher J. Moody
Keyword(s):  
Total Synthesis ◽  
Diazonamide A ◽  
Oxidative Rearrangement

scholarly journals Back Cover: Total Synthesis of (−)‐Salinosporamide A via a Late Stage C−H Insertion (Angew. Chem. Int. Ed. 30/2019)

2019 ◽  
Vol 58 (30) ◽  
pp. 10376-10376
Author(s):  
Hadi Gholami ◽  
Aman Kulshrestha ◽  
Olivia K. Favor ◽  
Richard J. Staples ◽  
Babak Borhan
Keyword(s):  
Total Synthesis ◽  
Late Stage ◽  
Back Cover ◽  
Salinosporamide A
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