scholarly journals Asymmetric Synthesis of Nodulones C & D by Chemoenzymatic Approach gives Insight into their Biosynthesis

2021 ◽  
Author(s):  
Tanaya Manna ◽  
Anshul Rajput ◽  
Nirmal Saha ◽  
Amit Mondal ◽  
Syed Masood Husain
Keyword(s):  
Secondary Metabolites ◽  
Total Synthesis ◽  
Asymmetric Synthesis ◽  
Magnaporthe Grisea ◽  
Asymmetric Total Synthesis ◽  
Related Enzyme ◽  
Insight Into ◽  
Fungal Secondary Metabolites

The first asymmetric total synthesis of fungal secondary metabolites, (R)-nodulone C (4) and trans-nodulone D (5) has been reported through the chemoenzymatic approach. The strategy utilizes NADPH-dependent naphthol reductases of Magnaporthe grisea for the reduction of putative biosynthetic substrates, synthesized non-enzymatically in multiple steps. A dihydronaphthalenone 32 and cis-nodulone D (30) has also been synthesized chemoenzymatically. The work implies for similar steps during the biosynthesis of nodulones and their analogs with the involvement of tetrahydroxynaphthalene reductase related enzyme(s).

Asymmetric total synthesis of (−)-δ-lycorane

2017 ◽  
Vol 4 (6) ◽  
pp. 1149-1152 ◽  
Author(s):  
Junliang Wang ◽  
Jianneng Li ◽  
Xianwang Shen ◽  
Cong Dong ◽  
Jun Lin ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Asymmetric Synthesis ◽  
Cascade Reaction ◽  
Asymmetric Total Synthesis

A first asymmetric synthesis of (−)-δ-lycorane by using a chiral bifunctional squaramide-catalysed cascade reaction is reported.

Asymmetric synthesis of machilin C and its analogue

2010 ◽  
Vol 64 (5) ◽  
Author(s):  
Yamu Xia ◽  
Wei Wang
Keyword(s):  
Total Synthesis ◽  
Asymmetric Synthesis ◽  
Absolute Configuration ◽  
Asymmetric Induction ◽  
Mitsunobu Reaction ◽  
Asymmetric Total Synthesis ◽  
Twelve Steps ◽  
The Absolute

AbstractFull details of the asymmetric total synthesis of erythro-8-O-4′-neolignan, machilin C, and its analogue perseal A are reported. The synthesis was involved in the Sharpless dihydroxylation reaction that occurred with excellent asymmetric induction, and the Mitsunobu reaction which occurred with inversion of the absolute configuration from the threo to the erythro isomer. The synthesis was achieved from simple vanillin in eight to twelve steps.

A concise asymmetric synthesis of (−)-trans-aerangis lactone

2018 ◽  
Vol 96 (12) ◽  
pp. 1061-1063 ◽  
Author(s):  
Rachana Pandey ◽  
Ranjana Prakash
Keyword(s):  
Ethylene Glycol ◽  
Total Synthesis ◽  
Asymmetric Synthesis ◽  
Aldol Reaction ◽  
Starting Material ◽  
Asymmetric Total Synthesis

A concise stereoselective approach to functionalized δ-lactone skeleton from monosilylated ethylene glycol as a starting material and its application to the asymmetric total synthesis of (−)-trans-aerangis lactone have been demonstrated. The synthesis utilizes the organocatalyzed MacMillan’s cross aldol reaction as a key step.

Asymmetric total synthesis of cephanolide B

2021 ◽  
Author(s):  
Hongyuan Zhang ◽  
Haibing He ◽  
Shuanhu Gao
Keyword(s):  
Total Synthesis ◽  
Asymmetric Synthesis ◽  
Asymmetric Total Synthesis ◽  
First Time

The asymmetric synthesis of cephanolide B, a complex C18 Cephalotaxus dinorditerpenoid, is presented for the first time.

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