Chiron approach for the total synthesis of brevipolide M

Synlett ◽  
2022 ◽  
Author(s):  
Yang Liu ◽  
Ziyang Zhao ◽  
Chao Hu ◽  
Chuanfang Zhao ◽  
Jun Liu ◽  
...  
Keyword(s):  
Double Bond ◽  
Total Synthesis ◽  
Stereoselective Synthesis ◽  
Ring Closing Metathesis ◽  
One Pot ◽  
Double Bond Migration ◽  
Key Steps

An efficient stereoselective synthesis of brevipolide M was established in 13 linear steps and 17.8% overall yields base on chiron approach. The key steps of our synthesis involved tandem homologation / tetrahydrofuran cyclization and sequential ring-closing metathesis (RCM) / double-bond migration in one-pot processes.

Concise Total Synthesis of Curvulone B

Synlett ◽  
2020 ◽  
Author(s):  
Debendra K. Mohapatra ◽  
Shivalal Banoth ◽  
Utkal Mani Choudhury ◽  
Kanakaraju Marumudi ◽  
Ajit C. Kunwar
Keyword(s):  
Total Synthesis ◽  
Stereoselective Synthesis ◽  
Ring System ◽  
Bond Forming ◽  
Cross Metathesis ◽  
Bond Forming Reactions ◽  
Key Steps

AbstractA concise and convergent stereoselective synthesis of curvulone B is described. The synthesis utilized a tandem isomerization followed by C–O and C–C bond-forming reactions following Mukaiyama-type aldol conditions for the construction of the trans-2,6-disubstituted dihydropyran ring system as the key steps. Other important features of this synthesis are a cross-metathesis, epimerization, and Friedel–Crafts acylation.

scholarly journals A short stereoselective synthesis of (+)-(6R,2′S)-cryptocaryalactone via ring-closing metathesis

2009 ◽  
Vol 5 ◽  
Author(s):  
Palakodety Radha Krishna ◽  
Krishnarao Lopinti ◽  
K L N Reddy
Keyword(s):  
Stereoselective Synthesis ◽  
Metathesis Reaction ◽  
Ring Closing Metathesis ◽  
Propargylic Alcohol ◽  
Key Steps

A short stereoselective synthesis of (+)-(6R,2′S)-cryptocaryalactone was successfully completed. Key steps included the application of Carreira’s asymmetric alkynylation reaction to form a propargylic alcohol and subsequently lactone formation using the powerful ring-closing metathesis reaction.

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.

Towards the Total Synthesis of Schisandrene: Stereoselective Synthesis of the Dibenzocyclooctadiene Lignan Core

Synlett ◽  
2018 ◽  
Vol 29 (07) ◽  
pp. 908-911 ◽  
Author(s):  
K. Babu ◽  
Arramshetti Venkanna ◽  
Borra Poornima ◽  
Bandi Siva ◽  
B. Babu
Keyword(s):  
Total Synthesis ◽  
Stereoselective Synthesis ◽  
Asymmetric Reduction ◽  
Cross Coupling ◽  
Membered Ring ◽  
Stille Reaction ◽  
Reaction Sequence ◽  
Ring Closing Metathesis ◽  
Synthetic Strategy ◽  
First Time

A stereoselective synthesis of the dibenzocyclooctadiene ­lignan core of the natural product schisandrene is described. Starting from readily available gallic acid, the synthetic strategy involves Suzuki–Miyaura cross-coupling, Stille reaction, and ring-closing metathesis (RCM) in the reaction sequence. The required asymmetric center at C-7′ was established by an asymmetric reduction of a keto compound using the Corey–Bakshi–Shibata (CBS) catalyst. In our approach, the eight-membered ring was achieved by RCM for the first time.

Total synthesis of haliclamide

2016 ◽  
Vol 14 (39) ◽  
pp. 9287-9293 ◽  
Author(s):  
Suraksha Gahalawat ◽  
Satyendra Kumar Pandey
Keyword(s):  
Total Synthesis ◽  
Stereoselective Synthesis ◽  
Steglich Esterification ◽  
Key Steps

A stereoselective synthesis of haliclamide has been developed. The synthesis includes MacMillan cross aldol, Mitsunobu inversion, Yamaguchi–Hirao alkylation, Steglich esterification and macrolactamization reactions and the Corey–Fuchs protocol as the key steps.

Total Synthesis of Amphidinolide X and Its 12Z-Isomer by Formation of the C12-C13 Trisubstituted Double Bond via Ring-Closing Metathesis

Synlett ◽  
2008 ◽  
Vol 2008 (11) ◽  
pp. 1737-1741 ◽  
Author(s):  
Wei-Min Dai ◽  
Jinlong Wu ◽  
Yile Chen ◽  
Jian Jin ◽  
Jianshu Lou ◽  
...  
Keyword(s):  
Double Bond ◽  
Total Synthesis ◽  
Ring Closing Metathesis ◽  
Trisubstituted Double Bond

scholarly journals A Concise and Stereoselective Total Synthesis of Paecilomycin E

2019 ◽  
Vol 14 (1) ◽  
pp. 1934578X1901400
Author(s):  
A. Srinivas Reddy ◽  
Gundamalla Bhavani ◽  
Sandhya Jonnala ◽  
Rajashaker Bantu ◽  
B. V. Subba Reddy
Keyword(s):  
Total Synthesis ◽  
Ring Closing Metathesis ◽  
Key Steps ◽  
Acid Unit

A concise approach for the first total synthesis of paecilomycin E is described involving Alder-Rickert reaction, Mitsunobu esterification and ring closing metathesis as the key steps. This approach has successfully demonstrated the Alder-Rickert protocol for the construction of resorcylic acid unit.

Synthesis of Carbocyclic Nucleosides (+)-Neplanocin A, (+)-Aristeromycin and 4'-epi-(+)-Aristeromycin from D-Fructose

2019 ◽  
Vol 16 (9) ◽  
pp. 750-758
Author(s):  
Perali R. Sridhar ◽  
Vennam D.K. Reddy ◽  
Mandava Suresh ◽  
Nadiveedhi M. Reddy ◽  
K. Shiva Kumar
Keyword(s):  
Total Synthesis ◽  
Allylic Alcohol ◽  
Starting Material ◽  
Carbocyclic Nucleosides ◽  
Ring Closing Metathesis ◽  
Neplanocin A ◽  
Oxidative Rearrangement ◽  
Key Steps

D-Fructose is used as the chiral pool starting material for the stereoselective total synthesis of (+)-neplanocin A. Zinc mediated fragmentation, ring-closing metathesis and oxidative rearrangement of cyclic tertiary allylic alcohol are used as the key steps in achieving the synthesis of key carbocylic intermediate. Further, stereoselective total synthesis of 4'-epi-(+)-aristeromycin and the conversion of (+)-neplanocin A to a mixture of (+)-aristeromycin and 4'-epi-(+)-aristeromycin are described.

Protecting-Group-Free Total Synthesis of Anticancer (±)-Melotenine A

Synthesis ◽  
2021 ◽  
Author(s):  
Adisak Thanetchaiyakup ◽  
Hassayaporn Rattanarat ◽  
Sudaporn Aree ◽  
Tanwawan Duangthongyou ◽  
Tanin Nanok ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Human Cancer ◽  
Alder Reaction ◽  
Diels Alder ◽  
Protecting Groups ◽  
Protecting Group ◽  
Ring Closing Metathesis ◽  
Human Cancer Cell Lines ◽  
Diels Alder Reaction ◽  
Key Steps

Melotenine A, isolated from Melodinus tenuicaudatus, possesses significant anticancer activity against several human cancer cell lines. The synthesis of (±)-melotenine A was achieved without the use of any protecting groups in 11 steps with an overall yield of 7%. The key steps of our strategy were the Diels–Alder reaction to construct the tetracyclic framework and ring-closing metathesis to form the seven-membered ring of (±)-melotenine A.

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