Formal total synthesis of (+)-stemoamide

Lycorane is a pentacyclic core presented in alkaloids isolated from the Amaryllidaceae family of herbaceous flowering plants. Members of this class of natural products have shown to display important biological properties including analgesic, antiviral, and antiproliferative activities. This review presents the known synthetic routes toward α‐, β‐, γ‐, and δ‐lycoranes. α‐(19 routes), β‐(10 routes), γ‐(38 routes), and δ‐(6 routes).

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“…Prasad et al [184] . documented a synthetic method for the synthesis of (+)‐γ‐lycorane taking advantage of Overman rearrangement [185,186] .…”

Section: Miscellaneousmentioning

confidence: 99%

Synthetic Approaches to α‐, β‐, γ‐, and δ‐Lycoranes

et al. 2023

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“…Pyne and Swamy exploited an ene–yne RCM to construct bicyclic species 12a en route to ent -1-hydroxystemoamide ( 12b ) (Scheme 6A). 34 Chavan and coworkers utilised an ene–ene RCM to synthesise bicycle 12c , 35 a which was transformed into tricycle 12d , a late-stage intermediate in Sibi and Subramanian's total synthesis of (−)-stemoamide (Scheme 6B). 36 A RCM has also been deployed to construct the A-ring in a formal synthesis of (+)-stemoamide ( 1a ).…”

Section: Synthesis Of Stemona Alkaloids and Related Compoundsmentioning

confidence: 99%

Strategies for the synthesis ofStemonaalkaloids: an update

et al. 2022

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“…[5] Stemoamide, first isolated from the roots and rhizomes of Stemonaceous plants, has been used in the treatment of respiratory diseases and also shows insecticidal activities. [6] The tetramic acid is a key natural product discovered from various terrestrial and marine organisms. [7] Most commonly observed are antimicrobial, antitumoral, antiviral, antiprotozoal, and antioxidant properties, with some compounds having multiple bioactivities reported.…”

Section: Introductionmentioning

confidence: 99%

“…Pramanicin was isolated from a fungus and has an antibacterial activity [5] . Stemoamide, first isolated from the roots and rhizomes of Stemonaceous plants, has been used in the treatment of respiratory diseases and also shows insecticidal activities [6] . The tetramic acid is a key natural product discovered from various terrestrial and marine organisms [7] .…”

Section: Introductionmentioning

confidence: 99%

Stereoselective Synthesis of Structurally Diverse (S)‐Lactams via an Engineered Amine Dehydrogenase

et al. 2022

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Optically pure lactams have a wide diversity of applications, one of which is serving as important intermediates in the synthesis of agricultural bioactive compounds or pharmaceuticals. Efficient stereoselective synthesis of chiral lactams with low‐cost amine donors under mild conditions is desired for manufacturing of these important chemicals. Herein, a two‐step chemo‐enzymatic strategy has been designed to produce (S)‐lactams by engineering a natural amine dehydrogenase from Thermoanaerobacter thermohydrosulfuricus (TtherAmDH). TtherAmDH was subjected to eight cycles of directed evolution to enhance its reductive amination activity toward keto acid substrates. The variants showed improved specific activity toward 6 tested substrates and gave high stereoselectivities of up to 99% in the asymmetric synthesis of γ‐ and δ‐ lactams. In particular, TtherAmDHV8 showed a 237‐fold higher specific activity toward the model substrate levulinic acid and gave (S)‐5‐methyl‐2‐pyrrolidone in 99% ee with a space‐time yield of 75.3 g L−1 d−1. These results indicate that the engineered amine dehydrogenase TtherAmDH can serve as an efficient biocatalyst for the manufacture of highly valued chiral lactams.

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Formal total synthesis of (+)-stemoamide

Cited by 10 publications

References 21 publications

Synthetic Approaches to α‐, β‐, γ‐, and δ‐Lycoranes

Synthetic Approaches to α‐, β‐, γ‐, and δ‐Lycoranes

Strategies for the synthesis ofStemonaalkaloids: an update

Stereoselective Synthesis of Structurally Diverse (S)‐Lactams via an Engineered Amine Dehydrogenase

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