Total synthesis of cytotoxic marine macrolides: Callipeltoside A, aurisides A and B, and dolastatin 19

2008 ◽  
Vol 80 (8) ◽  
pp. 1773-1782 ◽  
Author(s):  
Ian Paterson ◽  
Alison D. Findlay
Keyword(s):  
Total Synthesis ◽  
Conformational Analysis ◽  
Marine Origin ◽  
Total Syntheses ◽  
Stereochemical Assignment ◽  
Callipeltoside A ◽  
Marine Macrolides ◽  
Synthetic Studies

Synthetic studies pertaining to a novel class of structurally related glycosidic 14-membered macrolides of marine origin are reported. The evolution of a versatile aldol-based strategy that culminated in the total syntheses of callipeltoside A and aurisides A and B is detailed. Using a combination of biogenetic considerations and conformational analysis, a revised stereochemical assignment for the related polyketide dolastatin 19 was proposed and validated by total synthesis.

scholarly journals The Calyciphylline B-type Alkaloids: Total Syntheses of (–)-Daphlongamine H and (–)-Isodaphlongamine H

2019 ◽  
Author(s):  
Cedric Hugelshofer ◽  
Vignesh Palani ◽  
Richmond Sarpong
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Mannich Reaction ◽  
Biosynthetic Pathway ◽  
Total Syntheses ◽  
Diastereoselective Hydrogenation ◽  
Tricyclic Core ◽  
Synthetic Studies

The first total synthesis of the complex hexacylic Daphniphyllum alkaloid (–)-daphlongamine H in enantioenriched form has been accomplished. Key to the success of the strategy are a complexity-building Mannich reaction, efficient cyclizations, and a highly diastereoselective hydrogenation to assemble multigram quantities of the tricyclic core bearing four contiguous stereocenters. Following construction of the hydro-indene substructure by means of a Pauson–Khand reaction, endgame redox manipulations delivered the natural product. Importantly, the synthetic studies have also given access to (–)-isodaphlongamine H and led to a revision of the reported structure of deoxyisocalyciphylline B, which resulted in the proposal of a modified biosynthetic pathway to the calyciphylline B-type alkaloids.

scholarly journals The Calyciphylline B-type Alkaloids: Total Syntheses of (–)-Daphlongamine H and (–)-Isodaphlongamine H

2019 ◽  
Author(s):  
Cedric Hugelshofer ◽  
Vignesh Palani ◽  
Richmond Sarpong
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Mannich Reaction ◽  
Biosynthetic Pathway ◽  
Total Syntheses ◽  
Diastereoselective Hydrogenation ◽  
Tricyclic Core ◽  
Synthetic Studies

The first total synthesis of the complex hexacylic Daphniphyllum alkaloid (–)-daphlongamine H in enantioenriched form has been accomplished. Key to the success of the strategy are a complexity-building Mannich reaction, efficient cyclizations, and a highly diastereoselective hydrogenation to assemble multigram quantities of the tricyclic core bearing four contiguous stereocenters. Following construction of the hydro-indene substructure by means of a Pauson–Khand reaction, endgame redox manipulations delivered the natural product. Importantly, the synthetic studies have also given access to (–)-isodaphlongamine H and led to a revision of the reported structure of deoxyisocalyciphylline B, which resulted in the proposal of a modified biosynthetic pathway to the calyciphylline B-type alkaloids.

scholarly journals Recent Chemical Methodology Advances in the Total Synthesis of Meroterpenoids

2021 ◽  
Vol 68 (2) ◽  
pp. 247-267
Author(s):  
Jan Petrovčič ◽  
Chad Nicholas Ungarean ◽  
David Sarlah
Keyword(s):  
Organic Chemistry ◽  
Natural Products ◽  
Total Synthesis ◽  
Feature Article ◽  
Total Syntheses ◽  
Synthetic Organic Chemistry ◽  
Synthetic Studies

Heterogeneity of meroterpenoids arising from their dual biosynthetic origins is constantly provoking synthetic chemists to utilize their ingenuity and revise their retrosynthetic logic. By studying recent publications on meroterpenoid synthesis,tremendous advances in the field of synthetic organic chemistry can be witnessed. This feature article covers some of the most intriguing total syntheses and synthetic studies towards the meroterpenoid class of natural products from the last five years.

Synthetic studies on the A83586C and bryostatin antitumor macrolides and the monamycin antibiotics

2000 ◽  
Vol 72 (9) ◽  
pp. 1659-1670 ◽  
Author(s):  
K. J. Hale ◽  
M. G. Hummersone ◽  
J. Cai ◽  
S. Manaviazar ◽  
G. S. Bhatia ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Total Syntheses ◽  
Synthetic Studies ◽  
Synthetic Work

After a brief summary of our asymmetric total syntheses of A83586C and 4-epi-A83586C, we will go on to describe some of our synthetic work on the monamycins, and our most recent total synthesis studies on the bryostatin antitumor macrolides.

Isolation, Synthesis, and Biological Activity of Quindoline, a Valuable­ Indoloquinoline Natural Product and Useful Key Intermediate­

Synthesis ◽  
2018 ◽  
Vol 50 (07) ◽  
pp. 1417-1429 ◽  
Author(s):  
Teodoro Kaufman ◽  
María Méndez ◽  
Andrea Bracca
Keyword(s):  
Biological Activity ◽  
Total Synthesis ◽  
Natural Product ◽  
Natural Source ◽  
Total Syntheses ◽  
Naturally Occurring ◽  
The World ◽  
Biological Tests ◽  
Synthetic Studies

Quindoline is one of the simplest naturally occurring monomeric indoloquinoline alkaloids. Chemists exhibited interest in this compound before it was isolated from a natural source. The different approaches toward the total synthesis of the natural product and its performance in various biological tests are discussed. Aspects related to the isolation of quindoline from different ethnomedicinally relevant plants around the world are also reviewed.1 Introduction2 Isolation and Biogenetic Considerations3 Total Syntheses of Quindoline3.1 Early Synthetic Studies3.2 Syntheses from Benzenoids3.3 Syntheses from Indoles3.4 Syntheses from Quinolines4 Biological Activity Studies5 Conclusions

scholarly journals Synthesis and Biological Activities of Cyclodepsipeptides of Aurilide Family from Marine Origin

Marine Drugs ◽  
2021 ◽  
Vol 19 (2) ◽  
pp. 55
Author(s):  
Synthia Michon ◽  
Florine Cavelier ◽  
Xavier J. Salom-Roig
Keyword(s):  
Cell Lines ◽  
Cancer Cell ◽  
Biological Activities ◽  
Natural Compounds ◽  
Cancer Cell Lines ◽  
Hydroxy Ester ◽  
Marine Cyanobacteria ◽  
Synthetic Analogues ◽  
Marine Origin ◽  
Total Syntheses

Aurilides are a class of depsipeptides occurring mainly in marine cyanobacteria. Members of the aurilide family have shown to exhibit strong cytotoxicity against various cancer cell lines. These compounds bear a pentapeptide, a polyketide, and an α-hydroxy ester subunit in their structure. A large number of remarkable studies on aurilides have emerged since 1996. This comprehensive account summarizes the biological activities and total syntheses of natural compounds of the aurilide family as well as their synthetic analogues.

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