First Total Synthesis of 27-deoxylyngbyabellin A

Synthesis ◽  
2021 ◽  
Author(s):  
Yang Zhang ◽  
Yi Liu ◽  
Yuguo Du
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Secondary Metabolite ◽  
Building Block ◽  
Aldol Reaction ◽  
Cascade Reaction ◽  
Hydroxy Ester ◽  
Marine Cyanobacteria ◽  
One Pot ◽  
Key Steps

In this study, we documented the first total synthesis of marine cyanobacteria secondary metabolite 27-deoxylyngbyabellin A in 10 linear steps with 9.7% overall yield. Key steps entailed (1) one-pot cascade reaction of (S)-2-(benzyloxy)-3-methylbutanoic acid and Boc-Ile-Thz-OMe with the building block β-azido disulfide 7 to access the critical thiazole units 3 and 4, (2) chiral oxazaborolidinone-mediated asymmetry aldol reaction to construct (S)-β-hydroxy ester 5, and (3) DPPA-mediated macrolactamization of linear precursor 2 to achieve the natural product 27-deoxylyngbyabellin A.

Total Synthesis of (–)-Aristoquinoline via an Intramolecular Nitrilium Ion Cyclization

Synthesis ◽  
2021 ◽  
Author(s):  
Keith P. Reber ◽  
Priyansh D. Gujarati
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Building Block ◽  
Spectroscopic Properties ◽  
Ring System ◽  
Synthetic Route ◽  
Enantioselective Total Synthesis ◽  
Key Steps

AbstractThe enantioselective total synthesis of the alkaloid aristoquinoline has been achieved in seven steps and 26% overall yield. A new preparation of the useful synthetic building block (–)-α-terpinyl amine was also developed in order to avoid stoichiometric mercury reagents or azide-containing intermediates. Key steps in the optimized synthetic route include an intramolecular nitrilium ion cyclization to form the characteristic azabicyclo[3.3.1]nonane ring system and a dia­stereoselective reduction of the resulting imine mixture to afford the natural product. An isomer of aristoquinoline containing an exocyclic alkene was also obtained and found to exhibit unusual chromatographic and spectroscopic properties.

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.

First total synthesis of oteromycin utilizing one-pot four-step cascade reaction strategy

2013 ◽  
Vol 54 (6) ◽  
pp. 506-511 ◽  
Author(s):  
Hiromi Uchiro ◽  
Nobuhiro Shionozaki ◽  
Ryo Tanaka ◽  
Hiroyuki Kitano ◽  
Naoki Iwamura ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Cascade Reaction ◽  
One Pot

scholarly journals Stereoselective Total Synthesis of (6S)-5,6-Dihydro-6-[(2R)-2-hydroxy-6-phenylhexyl]-2H-pyran-2-one from L-Malic Acid

2018 ◽  
Vol 13 (7) ◽  
pp. 1934578X1801300
Author(s):  
Dandekar Chandrakanth ◽  
Yerragorla Gopala Rao ◽  
Tallapally Swamy ◽  
Dhanraj O Biradar ◽  
Lonavath Vishnupriya ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Malic Acid ◽  
Ring Closing Metathesis ◽  
Stereoselective Reduction ◽  
Key Steps ◽  
Barbier Allylation

A stereoselective total synthesis of an antiproliferative and antifungal natural product, (6 S)-5,6-dihydro-6-[(2 R)-2-hydroxy-6-phenylhexyl]-2 H-pyran-2-one has been accomplished using the Barbier allylation, LiAlH4/LiI mediated syn-stereoselective reduction and olefin ring-closing metathesis (RCM) as the key steps. L-Malic acid was used as a chiral precursor for the construction of syn-1,3-diol moiety of the molecule.

ChemInform Abstract: Total Synthesis of Aristolactams via a One-Pot Suzuki-Miyaura Coupling/Aldol Condensation Cascade Reaction.

ChemInform ◽  
2008 ◽  
Vol 39 (51) ◽  
Author(s):  
Joa Kyum Kim ◽  
Young Ha Kim ◽  
Ho Tae Nam ◽  
Bum Tae Kim ◽  
Jung-Nyoung Heo
Keyword(s):  
Total Synthesis ◽  
Aldol Condensation ◽  
Cascade Reaction ◽  
One Pot

An efficient catalyst-free Mukaiyama-aldol reaction of fluorinated enol silyl ethers with tryptanthrin

2015 ◽  
Vol 13 (33) ◽  
pp. 8906-8911 ◽  
Author(s):  
Fu-Min Liao ◽  
Yun-Lin Liu ◽  
Jin-Sheng Yu ◽  
Feng Zhou ◽  
Jian Zhou
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Aldol Reaction ◽  
Efficient Catalyst ◽  
Silyl Ethers ◽  
Mukaiyama Aldol Reaction ◽  
Catalyst Free ◽  
Mukaiyama Aldol ◽  
Enol Silyl Ethers ◽  
Fluoroalkyl Group

We report an efficient Mukaiyama-aldol reaction of tryptanthrin with fluorinated enol silyl ethers, which is carried out in methanol without the use of any catalyst. This represents the first modification of tryptanthrin by a fluoroalkyl group, which is applied to the total synthesis of the difluoro analogues of the natural product Phaitanthrin B.

The Structure Elucidation of Haprolid

Synthesis ◽  
2017 ◽  
Vol 50 (03) ◽  
pp. 529-538 ◽  
Author(s):  
Markus Kalesse ◽  
Jun Li ◽  
Jun Xing ◽  
Daniel Lücke ◽  
Dennis Lübken ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Structure Elucidation ◽  
Carcinoma Cell ◽  
Hidden Markov ◽  
Biological Evaluation ◽  
Terminal Olefin ◽  
Carcinoma Cell Lines ◽  
Hepatocellular Carcinoma Cell ◽  
Key Steps

The assignment of two stereocenters of the natural product haprolid through the application of a profile hidden Markov model (HMM) and its confirmation through total synthesis of the natural product and of two of its diastereomers are reported. The structure elucidation of this polyketide-peptide hybrid natural product is a telling showcase of how difficult it can be to determine the absolute configuration of isolated stereocenters and the benefits of a gene cluster analysis for structure determination. The key steps of the synthesis are a selective epoxidation of a terminal olefin and the stereodivergent macrolactonization strategy. Furthermore, the biological evaluation of all products showed that all diastereomers are potent inhibitors of hepatocellular carcinoma cell lines.

Enantioselective total synthesis of (S)-nakinadine B

RSC Advances ◽  
2016 ◽  
Vol 6 (31) ◽  
pp. 25913-25917 ◽  
Author(s):  
Yuvraj Garg ◽  
Satyendra Kumar Pandey
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Michael Addition ◽  
Marine Natural Product ◽  
Enantioselective Total Synthesis ◽  
Novel Approach ◽  
Key Steps

A novel approach for the synthesis of (S)-nakinadine B, a marine natural product is described. The synthesis utilizes the optimized combination of organocatalyzed Michael addition and aminoxylation reactions as key steps.

Sign in / Sign up

Export Citation Format

Share Document