A General Strategy for the Synthesis of Vincamajine-Related Indole Alkaloids:  Stereocontrolled Total Synthesis of (+)-Dehydrovoachalotine, (−)-Vincamajinine, and (−)-11-Methoxy-17-epivincamajine as Well as the Related Quebrachidine Diol, Vincamajine Diol, and Vincarinol1

2005 ◽  
Vol 70 (10) ◽  
pp. 3963-3979 ◽  
Author(s):  
Jianming Yu ◽  
Xiangyu Z. Wearing ◽  
James M. Cook
Keyword(s):  
Total Synthesis ◽  
Indole Alkaloids ◽  
General Strategy

A One-Pot Chemoenzymatic Synthesis of (2S,4R)-4-Methylproline Enables the First Total Synthesis of Antiviral Lipopeptide Cavinafungin B

2018 ◽  
Author(s):  
Christian R. Zwick ◽  
Hans Renata
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Complex Molecule ◽  
Molecular Target ◽  
Chemoenzymatic Synthesis ◽  
General Strategy ◽  
One Pot

We report an efficient ten-step synthesis of antiviral natural product cavinafungin B in 37% overall yield. By leveraging a one-pot chemoenzymatic synthesis of (2S,4R)-4-methylproline and oxazolidine-tethered (Rink-Boc-ATG-resin) SPPS methodology, the assembly of our molecular target could be conducted in an efficient manner.This general strategy could prove amenable to the construction of other natural and unnatural linear lipopeptides. The value of incorporating biocatalytic steps in complex molecule synthesis is highlighted by this work.

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>

Recent advances in hapalindole-type cyanobacterial alkaloids: biosynthesis, synthesis, and biological activity

2021 ◽  
Author(s):  
Robert M. Hohlman ◽  
David H. Sherman
Keyword(s):  
Biological Activity ◽  
Total Synthesis ◽  
Indole Alkaloids ◽  
Recent Advances

This review covers isolation, biological activity, an overview of total synthesis efforts and recent biosynthetic discoveries related to hapalindole-type indole alkaloids.

scholarly journals The chemistry of mavacurane alkaloids: a rich source of bis-indole alkaloids

2021 ◽  
Author(s):  
Audrey Mauger ◽  
Maxime Jarret ◽  
Cyrille Kouklovsky ◽  
Erwan Poupon ◽  
Laurent Evanno ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Indole Alkaloids ◽  
Rich Source ◽  
Monoterpene Indole Alkaloids

This review presents the chemistry of mavacuranes, a subfamily of the monoterpene indole alkaloids, from their isolation, biosynthesis, total synthesis to their tendency to assemble with other partners to form intricate bis-indole alkaloids.

ChemInform Abstract: Total Synthesis of Both (+)-Compactin and (+)-Mevinolin. A General Strategy Based on the Use of a Special TiCl3/C8K Mixture for Dicarbonyl Coupling.

ChemInform ◽  
1989 ◽  
Vol 20 (3) ◽  
Author(s):  
D. L. J. CLIVE ◽  
K. S. K. MURTHY ◽  
A. G. H. WEE ◽  
J. S. PRASAD ◽  
G. V. J. DA SILVA ◽  
...  
Keyword(s):  
Total Synthesis ◽  
General Strategy

Studies Towards the Total Synthesis of Cycloaraneosene and Ophiobolin M: A General Strategy for the Construction of the 5−8 Bicyclic Ring System

2002 ◽  
Vol 2002 (18) ◽  
pp. 3145-3152 ◽  
Author(s):  
Parminder K. Ruprah ◽  
Jean-Philippe Cros ◽  
J. Elizabeth Pease ◽  
William G Whittingham ◽  
Jonathan M. J. Williams
Keyword(s):  
Total Synthesis ◽  
Ring System ◽  
General Strategy

ChemInform Abstract: Total Synthesis of the Indole Alkaloids Henrycinol A (Ia) and B (Ib).

ChemInform ◽  
2014 ◽  
Vol 45 (51) ◽  
pp. no-no
Author(s):  
Kavirayani R. Prasad ◽  
John Eugene Nidhiry ◽  
Makuteswaran Sridharan
Keyword(s):  
Total Synthesis ◽  
Indole Alkaloids
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