Stereoselective total synthesis of (+)-strictifolione and (6R)-6-[(4R,6R)-4,6-dihydroxy-10-phenyldec-1-enyl]-5,6-dihydro-2H-pyran-2-one by Prins reaction and olefin cross-metathesis

Sabitha, Gowravaram; Fatima, Narjis; Gopal, Peddabuddi; Reddy, Chintam Nagendra; Yadav, J. S.

doi:10.1016/j.tetasy.2008.12.004

Cited by 36 publications

(11 citation statements)

References 25 publications

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“…Its earlier syntheses were mentioned by Macro et al [12]. Recently, a large number of new syntheses of strictifolione (176) have been reported [92,[103][104][105][106][107][108][109].…”

Section: Strictifolionementioning

confidence: 98%

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Recent Advances in the Stereoselective Total Synthesis of Natural Pyranones Having Long Side Chains

et al. 2020

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Pyranone natural products have attracted great attention in recent years from chemists and biologists due to their fascinating stereoisomeric structural features and impressive bioactivities. A large number of stereoselective total syntheses of these compounds have been described in the literature. The natural pyranones with long side chains have recently received significant importance in the synthetic field. In the present article, we aim to review the modern progress of the stereoselective total syntheses of these natural pyranones containing long-chain substituents.

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“…Its earlier syntheses were mentioned by Macro et al [12]. Recently, a large number of new syntheses of strictifolione (176) have been reported [92,[103][104][105][106][107][108][109].…”

Section: Strictifolionementioning

confidence: 98%

“…In a recent synthesis, known chiral allyl alcohol 177 was used as a starting material (Scheme 35) [103]. The Prins reaction between 177 and benzaldehyde followed by hydrolysis of the generated trifluoroacetate and protection of the hydroxyl group afforded 178.…”

Section: Strictifolionementioning

confidence: 99%

Recent Advances in the Stereoselective Total Synthesis of Natural Pyranones Having Long Side Chains

et al. 2020

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“…In continuation of our interest in the synthesis of biologically active δ ‐lactone‐containing natural products, we herein describe our synthetic studies toward phostriecin ( 1 ), goniothalamins, and their derivatives. Our study mainly aimed at developing a suitable methodology for the synthesis of 5‐hydroxy‐vinyl‐lactone (C1–C7 unit) and its application in the synthesis of several biologically active molecules such as phostriecin, 5‐hydroxygoniothalamin, and 5‐acetoxygoniothalamin by using a cross‐metathesis reaction as the key step.…”

Section: Introductionmentioning

confidence: 99%

Stereoselective Synthesis of C1–C7 and C6–C22 Fragments of Phostriecin, Goniothalamines, and Their Analogues

Reddy

Sabitha

2018

Eur J Org Chem

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“…It is either possible to synthesize the δ-lactone in a linear sequence or the vinyl lactone 2 (Figure 1) can be synthesized from another chiral pool derived starting material. 6 In this case, both building blocks are then connected via cross metathesis. We envisaged a first asymmetric synthesis of the title natural product employing a chiral auxiliary approach.…”

mentioning

confidence: 99%

“…1 H NMR (600 MHz, CDCl 3 ): δ = 1.17 (d, 3 J = 6.6 Hz,3 H,CH 3 ), 2.01 (s, 3 H, CH 3 ), 2.04 (s, 3 H, CH 3 ), 2.14 (s, 3 H, CH 3 ), 2.52-2.66 (m, 2 H, CH 2 ), 5.12 (dd, 3 J = 3.1 Hz, 3 J = 8.0 Hz, 1 H, CH), 5.15-5.22 (m, 2 H, 2 × CH), 6.11 (ddt, 4 J = 1.2 Hz, 3 J = 7.7 Hz, 3 J = 15. 6 Hz, 1 H, CH), 6.72 (ddd, 3 J = 6.9 Hz, 3 J = 7.5 Hz, 3 J = 15.6 Hz, 1 H, CH), 9.49 (d, 3 J = 7.7 Hz, 1 H, CHO). 13…”

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confidence: 99%

Asymmetric Synthesis of Synargentolide A and Its 3-Epimer Using the RAMP-Hydrazone Methodology

Enders

Reichenbach

2013

Synthesis

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Synargentolide A was synthesized in 11 steps starting from the commercially available 2,2-dimethyl-1,3-dioxan-5-one, employing the SAMP/RAMP-methodology via an α,α′-bis-alkylation to generate the first two stereogenic centers with virtually complete asymmetric induction (de, ee >99%). After the asymmetric synthesis of the triol fragment of the molecule, the δ-lactone moiety was constructed using an asymmetric allylation, esterification, and ring-closing metathesis sequence.Synargentolide A (1a) was first extracted by Rivett et al. in 1997 from the aerial parts of the South African plant Syncolestemon argenteus, found in the Ongoya forest in the Kwazulu-Natal midlands. 1 α,β-Unsaturated 6-substituted δ-lactones like synargentolide A are interesting targets in the field of natural product synthesis due to their biological activity. 2 Cytotoxity, antitumor activity, HIVprotease inhibition, and antileukemic activity are only some of the pharmacological properties that have been proven for related compounds so far. 3The published structure of synargentolide A (1b) was first synthesized by Marco et al. in 2005. 4 This structure proved to have one misassigned stereocenter. The revised structure 1a (Figure 1) was later synthesized by several groups. These published syntheses share the common feature that at least one of the stereogenic centers on the triol moiety of the molecule is part of a starting material derived from the chiral pool. 5 Figure 1 Structure of synargentolide A and a δ-lactone building block 2Once the polyacetylated triol chain of the target molecule is synthesized, two strategies have been employed. It is either possible to synthesize the δ-lactone in a linear sequence or the vinyl lactone 2 (Figure 1) can be synthesized from another chiral pool derived starting material. 6 In this case, both building blocks are then connected via cross metathesis. We envisaged a first asymmetric synthesis of the title natural product employing a chiral auxiliary approach. As the retrosynthetic analysis in Scheme 1 shows, synargentolide A can be traced back to the commercially available and easily synthesized 2,2-dimethyl-1,3-dioxan-5-one (3) 7 via a ring-closing cross-metathesis α,α′-bis-alkylation sequence. 8 Scheme 1 Retrosynthesis analysis for synargentolide AWe now wish to present a first asymmetric synthesis of synargentolide A employing the SAMP/RAMP-hydrazone methodology to create the first two stereogenic centers (Scheme 2). First the RAMP-hydrazone 4 of the dioxanone 3 was synthesized according to the literature procedure in excellent yield (98%). 9

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Stereoselective total synthesis of (+)-strictifolione and (6R)-6-[(4R,6R)-4,6-dihydroxy-10-phenyldec-1-enyl]-5,6-dihydro-2H-pyran-2-one by Prins reaction and olefin cross-metathesis

Cited by 36 publications

References 25 publications

Recent Advances in the Stereoselective Total Synthesis of Natural Pyranones Having Long Side Chains

Recent Advances in the Stereoselective Total Synthesis of Natural Pyranones Having Long Side Chains

Stereoselective Synthesis of C1–C7 and C6–C22 Fragments of Phostriecin, Goniothalamines, and Their Analogues

Asymmetric Synthesis of Synargentolide A and Its 3-Epimer Using the RAMP-Hydrazone Methodology

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